NPASS Compound

Structure

CID5989 OpenBabel06191715332D 44 47 0 0 1 0 0 0 0 0999 V2000 12.0781 3.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2047 3.6680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3463 3.1551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4729 3.6421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6144 3.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7410 3.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8825 3.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0091 3.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1507 3.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2773 3.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4188 3.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 -0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 -2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 33 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 29 1 0 0 0 0 19 23 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 22 37 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 24 35 1 1 0 0 0 25 38 2 0 0 0 0 25 44 1 0 0 0 0 27 30 1 0 0 0 0 27 35 1 1 0 0 0 28 34 1 6 0 0 0 28 35 1 0 0 0 0 29 39 2 0 0 0 0 29 43 1 0 0 0 0 30 33 1 0 0 0 0 30 36 1 6 0 0 0 31 34 1 0 0 0 0 31 40 2 0 0 0 0 32 36 1 6 0 0 0 32 43 1 0 0 0 0 33 36 1 0 0 0 0 34 41 1 6 0 0 0 35 42 1 1 0 0 0 36 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.21
Volume:	408.827
LogP:	6.735
LogD:	4.132
LogS:	-3.558
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	4.707
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778
MDCK Permeability:	1.555218841531314e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	100.40033721923828%
Volume Distribution (VD):	2.252
Pgp-substrate:	3.3590614795684814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.322
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	0.859
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.691
Skin Sensitization:	0.472
Carcinogencity:	0.645
Eye Corrosion:	0.004
Eye Irritation:	0.463
Respiratory Toxicity:	0.968

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC5989

Natural Product ID:	NPC5989
*Common Name:**	Phorbol Myristate Acetate
IUPAC Name:	n.a.
Synonyms:	Phorbol Myristate Acetate
Standard InCHIKey:	PHEDXBVPIONUQT-RGYGYFBISA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
SMILES:	CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL279115
PubChem CID:	27924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520228]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO40906	Peruvian amazonian	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18163590]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO13882	Euphorbia grandicornis	Species	Euphorbiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21319774]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[21520897]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23148674]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23215460]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO13882	Euphorbia grandicornis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27731641]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO21274	Euphorbia semiperfoliata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28925702]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO4152	Oleum linderae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29390	Semen juglandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO7170	Tylophora ovata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16841	Elsholtzia bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29390	Semen juglandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4152	Oleum linderae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7170	Tylophora ovata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21274	Euphorbia semiperfoliata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16841	Elsholtzia bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13882	Euphorbia grandicornis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	17
ED50	1
GI50	2
IC50	13
Ki	7
Others	58
Potency	9

Activity Type	# Activity
Cell Line	20
Individual Protein	27
NON-MOLECULAR	5
Organism	29
Others	21
Protein Family	2
Protein-Protein Interaction	1
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Ki	=	2.5	nM	PMID[504346]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	1.32	nM min-1 ml-1	PMID[504348]
NPT466	Cell Line	U-937	Homo sapiens	EC50	=	0.45	nM	PMID[504349]
NPT886	Cell Line	NIH3T3	Mus musculus	GI50	=	0.01	ug.mL-1	PMID[504352]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	0.00012	ug.mL-1	PMID[504352]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	3.0	nM	PMID[504358]
NPT116	Cell Line	HL-60	Homo sapiens	ED100	=	6.0	nM	PMID[504358]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	50.0	%	PMID[504364]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[504364]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	63095.7	nM	PMID[504366]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[504366]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	10000.0	nM	PMID[504366]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Ki	=	6.4	nM	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	108.43	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	100.0	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	85.31	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	80.64	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	62.39	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	11.14	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Activity	=	0.58	%	PMID[504367]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	EC50	=	1700000.0	nM	PMID[504369]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[504366]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	19.61	%	PMID[504373]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	5700.0	nM	PMID[504374]
NPT890	Cell Line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[504376]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[504377]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	50.0	%	PMID[504377]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	891.3	nM	PMID[504366]
NPT891	Cell Line	iNKT		Activity	=	8.5	%	PMID[504380]
NPT466	Cell Line	U-937	Homo sapiens	GI	=	50.0	%	PMID[504382]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	38.1	%	PMID[504385]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	120.0	%	PMID[504387]
NPT2740	Cell Line	Neutrophils		Activity	=	44.2	%	PMID[504389]
NPT2740	Cell Line	Neutrophils		Activity	=	102.7	%	PMID[504389]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	5700.0	nM	PMID[504390]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	120.0	%	PMID[504392]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	EC50	=	10.0	nM	PMID[504393]
NPT2	Others	Unspecified		IC50	=	10.0	nM	PMID[504344]
NPT32	Organism	Mus musculus	Mus musculus	Epidermal thickness	=	62.2	n.a.	PMID[504345]
NPT760	Individual Protein	Protein kinase C beta	Homo sapiens	Ki	=	1.8	nM	PMID[504346]
NPT880	Individual Protein	Protein kinase C gamma	Homo sapiens	Ki	=	4.9	nM	PMID[504346]
NPT881	Individual Protein	Protein kinase C delta	Homo sapiens	Ki	=	0.8	nM	PMID[504346]
NPT761	Individual Protein	Protein kinase C epsilon	Homo sapiens	Ki	=	0.45	nM	PMID[504346]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	Activity	=	899.0	pM min-1 (mg of protein)-1	PMID[504347]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	0.85	nM	PMID[504349]
NPT2	Others	Unspecified		Activity	=	97.3	%	PMID[504351]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.016	nmol	PMID[504353]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.05	ug	PMID[504353]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	63.0	/nmol	PMID[504353]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.0085	ug	PMID[504355]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.012	ug	PMID[504355]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.04	ug	PMID[504357]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.05	ug	PMID[504357]
NPT2	Others	Unspecified		IC50	=	15.0	nM	PMID[504358]
NPT2	Others	Unspecified		ED50	=	15.0	nM	PMID[504358]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	93.3	%	PMID[504358]
NPT881	Individual Protein	Protein kinase C delta	Homo sapiens	EC50	=	5170.0	nM	PMID[504359]
NPT761	Individual Protein	Protein kinase C epsilon	Homo sapiens	EC50	=	5560.0	nM	PMID[504359]
NPT887	Individual Protein	Protein kinase C theta	Homo sapiens	EC50	=	3190.0	nM	PMID[504359]
NPT610	Others	Molecular identity unknown		Inhibition	=	21.3	%	PMID[504361]
NPT610	Others	Molecular identity unknown		Inhibition	=	18.3	%	PMID[504361]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10000.0	nM	PMID[504363]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6309.57	nM	PMID[504363]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12589.25	nM	PMID[504363]
NPT2	Others	Unspecified		Activity	=	30.2	%	PMID[504364]
NPT2	Others	Unspecified		Activity	=	28.8	%	PMID[504364]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	Survival	=	26.0	%	PMID[504365]
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PMID[504366]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[504366]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[504366]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	100.0	%	PMID[504372]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-6.35	%	PMID[504373]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	162000.0	nM	PMID[504374]
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	=	2200.0	nM	PMID[504374]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1965.0	n.a.	PMID[504374]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2.9	nM	PMID[504374]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	31.5	%	PMID[504377]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	29.4	%	PMID[504377]
NPT2	Others	Unspecified		Ki	=	0.59	nM	PMID[504378]
NPT2	Others	Unspecified		IC50	=	0.79	nM	PMID[504378]
NPT2	Others	Unspecified		Inhibition	=	-1.0	%	PMID[504378]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[504366]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1965.0	n.a.	PMID[504383]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2.9	nM	PMID[504383]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	220.0	n.a.	PMID[504383]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.9	nM	PMID[504383]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	0.7	nM	PMID[504383]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	107377.0	n.a.	PMID[504383]
NPT610	Others	Molecular identity unknown		Activity	=	39.2	%	PMID[504385]
NPT610	Others	Molecular identity unknown		Activity	=	25.0	%	PMID[504385]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	120.0	%	PMID[504386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	420.0	%	PMID[504386]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	EC50	=	9.5	nM	PMID[504388]
NPT20632	ORGANISM	Chikungunya virus	Chikungunya virus	EC50	=	2.9	nM	PMID[504390]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1965.0	n.a.	PMID[504390]
NPT25273	SINGLE PROTEIN	RAS guanyl releasing protein 3	Homo sapiens	EC50	=	82.0	nM	PMID[504391]
NPT881	Individual Protein	Protein kinase C delta	Homo sapiens	EC50	=	290.0	nM	PMID[504391]
NPT2	Others	Unspecified		Ratio EC50	=	3.5	n.a.	PMID[504391]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.07	%	PMID[504394]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.61	%	PMID[504395]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[504397]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[504397]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC5989 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1483
0.2-0.3	4493
0.3-0.4	7418
0.4-0.5	13814
0.5-0.6	7902
0.6-0.7	5885
0.7-0.8	1300
0.8-0.85	30
0.85-0.9	30
0.9-0.95	54
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471108
1.0	High Similarity	NPC22628
1.0	High Similarity	NPC5991
1.0	High Similarity	NPC275696
1.0	High Similarity	NPC255081
0.9908	High Similarity	NPC171905
0.9908	High Similarity	NPC472397
0.9908	High Similarity	NPC472758
0.9908	High Similarity	NPC471125
0.982	High Similarity	NPC52839
0.9732	High Similarity	NPC19464
0.973	High Similarity	NPC471128
0.973	High Similarity	NPC471126
0.973	High Similarity	NPC145182
0.973	High Similarity	NPC157252
0.9643	High Similarity	NPC472401
0.9636	High Similarity	NPC156252
0.9561	High Similarity	NPC145238
0.9558	High Similarity	NPC162009
0.9558	High Similarity	NPC257017
0.9541	High Similarity	NPC472757
0.9474	High Similarity	NPC472399
0.9459	High Similarity	NPC10721
0.9455	High Similarity	NPC472400
0.9369	High Similarity	NPC471127
0.9369	High Similarity	NPC154363
0.9369	High Similarity	NPC234858
0.9358	High Similarity	NPC475937
0.9358	High Similarity	NPC158523
0.9286	High Similarity	NPC153651
0.9279	High Similarity	NPC474872
0.9266	High Similarity	NPC153036
0.9211	High Similarity	NPC472759
0.9211	High Similarity	NPC329080
0.9211	High Similarity	NPC185876
0.9211	High Similarity	NPC19336
0.9204	High Similarity	NPC124676
0.9204	High Similarity	NPC146280
0.9189	High Similarity	NPC71889
0.9189	High Similarity	NPC474937
0.9123	High Similarity	NPC236918
0.9123	High Similarity	NPC180640
0.9123	High Similarity	NPC156745
0.9099	High Similarity	NPC215643
0.9099	High Similarity	NPC89227
0.9099	High Similarity	NPC101825
0.9099	High Similarity	NPC170212
0.9099	High Similarity	NPC151216
0.9099	High Similarity	NPC265499
0.9099	High Similarity	NPC221511
0.9099	High Similarity	NPC17138
0.9099	High Similarity	NPC475391
0.9043	High Similarity	NPC475885
0.9035	High Similarity	NPC472760
0.9018	High Similarity	NPC477091
0.9009	High Similarity	NPC260786
0.9009	High Similarity	NPC174471
0.9009	High Similarity	NPC474871
0.9009	High Similarity	NPC96739
0.9	High Similarity	NPC163004
0.8992	High Similarity	NPC270109
0.8898	High Similarity	NPC473919
0.8898	High Similarity	NPC473709
0.8824	High Similarity	NPC222307
0.8814	High Similarity	NPC473802
0.875	High Similarity	NPC471940
0.8678	High Similarity	NPC236999
0.8667	High Similarity	NPC471939
0.864	High Similarity	NPC243902
0.8475	Intermediate Similarity	NPC472667
0.8417	Intermediate Similarity	NPC222688
0.8376	Intermediate Similarity	NPC179626
0.8333	Intermediate Similarity	NPC273433
0.832	Intermediate Similarity	NPC90814
0.832	Intermediate Similarity	NPC180902
0.832	Intermediate Similarity	NPC475139
0.832	Intermediate Similarity	NPC189393
0.8254	Intermediate Similarity	NPC476111
0.825	Intermediate Similarity	NPC143755
0.8235	Intermediate Similarity	NPC251310
0.8189	Intermediate Similarity	NPC100017
0.8189	Intermediate Similarity	NPC476823
0.8189	Intermediate Similarity	NPC182266
0.8189	Intermediate Similarity	NPC471137
0.8189	Intermediate Similarity	NPC475500
0.8189	Intermediate Similarity	NPC223356
0.8189	Intermediate Similarity	NPC473548
0.8189	Intermediate Similarity	NPC471136
0.8189	Intermediate Similarity	NPC475154
0.8182	Intermediate Similarity	NPC310511
0.816	Intermediate Similarity	NPC162495
0.8151	Intermediate Similarity	NPC471854
0.8145	Intermediate Similarity	NPC168849
0.8145	Intermediate Similarity	NPC475273
0.8136	Intermediate Similarity	NPC473798
0.812	Intermediate Similarity	NPC472002
0.812	Intermediate Similarity	NPC474516
0.811	Intermediate Similarity	NPC469673
0.8095	Intermediate Similarity	NPC196921
0.8095	Intermediate Similarity	NPC220757
0.808	Intermediate Similarity	NPC470850
0.807	Intermediate Similarity	NPC60315
0.8067	Intermediate Similarity	NPC96312
0.8067	Intermediate Similarity	NPC474734
0.8067	Intermediate Similarity	NPC470793
0.8067	Intermediate Similarity	NPC40632
0.8067	Intermediate Similarity	NPC328374
0.8067	Intermediate Similarity	NPC270958
0.8067	Intermediate Similarity	NPC251236
0.8065	Intermediate Similarity	NPC217901
0.8065	Intermediate Similarity	NPC15095
0.8062	Intermediate Similarity	NPC68282
0.8053	Intermediate Similarity	NPC475623
0.8053	Intermediate Similarity	NPC473694
0.8053	Intermediate Similarity	NPC475334
0.8051	Intermediate Similarity	NPC49451
0.8051	Intermediate Similarity	NPC477126
0.8051	Intermediate Similarity	NPC202889
0.8051	Intermediate Similarity	NPC108721
0.8051	Intermediate Similarity	NPC73300
0.8051	Intermediate Similarity	NPC962
0.8051	Intermediate Similarity	NPC250109
0.8034	Intermediate Similarity	NPC475668
0.8034	Intermediate Similarity	NPC475480
0.8034	Intermediate Similarity	NPC473921
0.8031	Intermediate Similarity	NPC474508
0.8031	Intermediate Similarity	NPC473485
0.8031	Intermediate Similarity	NPC34963
0.8017	Intermediate Similarity	NPC472933
0.8017	Intermediate Similarity	NPC469380
0.8016	Intermediate Similarity	NPC470851
0.8016	Intermediate Similarity	NPC104382
0.8016	Intermediate Similarity	NPC35109
0.8	Intermediate Similarity	NPC122033
0.8	Intermediate Similarity	NPC470854
0.8	Intermediate Similarity	NPC143609
0.8	Intermediate Similarity	NPC474654
0.8	Intermediate Similarity	NPC67321
0.8	Intermediate Similarity	NPC470882
0.8	Intermediate Similarity	NPC470775
0.8	Intermediate Similarity	NPC176513
0.8	Intermediate Similarity	NPC97908
0.8	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC287343
0.7982	Intermediate Similarity	NPC181104
0.7982	Intermediate Similarity	NPC201144
0.7982	Intermediate Similarity	NPC475331
0.7982	Intermediate Similarity	NPC288502
0.7982	Intermediate Similarity	NPC121518
0.7982	Intermediate Similarity	NPC103298
0.7982	Intermediate Similarity	NPC80809
0.7982	Intermediate Similarity	NPC475335
0.7969	Intermediate Similarity	NPC58029
0.7966	Intermediate Similarity	NPC280782
0.7966	Intermediate Similarity	NPC71348
0.7966	Intermediate Similarity	NPC317687
0.7966	Intermediate Similarity	NPC234042
0.7966	Intermediate Similarity	NPC152117
0.7953	Intermediate Similarity	NPC251564
0.7953	Intermediate Similarity	NPC241935
0.7953	Intermediate Similarity	NPC475606
0.7953	Intermediate Similarity	NPC471170
0.7953	Intermediate Similarity	NPC477189
0.7953	Intermediate Similarity	NPC279478
0.7953	Intermediate Similarity	NPC475314
0.7951	Intermediate Similarity	NPC4548
0.7951	Intermediate Similarity	NPC472004
0.7951	Intermediate Similarity	NPC112038
0.7951	Intermediate Similarity	NPC109973
0.7949	Intermediate Similarity	NPC257240
0.7949	Intermediate Similarity	NPC477103
0.7949	Intermediate Similarity	NPC5103
0.7949	Intermediate Similarity	NPC475563
0.7949	Intermediate Similarity	NPC475134
0.7946	Intermediate Similarity	NPC470074
0.7934	Intermediate Similarity	NPC257457
0.7934	Intermediate Similarity	NPC118638
0.7934	Intermediate Similarity	NPC311554
0.7931	Intermediate Similarity	NPC29827
0.7931	Intermediate Similarity	NPC476479
0.792	Intermediate Similarity	NPC225049
0.792	Intermediate Similarity	NPC473635
0.792	Intermediate Similarity	NPC293112
0.7917	Intermediate Similarity	NPC49492
0.7917	Intermediate Similarity	NPC148458
0.7917	Intermediate Similarity	NPC266728
0.7913	Intermediate Similarity	NPC111952
0.7903	Intermediate Similarity	NPC67251
0.7899	Intermediate Similarity	NPC469463
0.7899	Intermediate Similarity	NPC469454
0.7899	Intermediate Similarity	NPC208998
0.7899	Intermediate Similarity	NPC7921
0.7899	Intermediate Similarity	NPC469496
0.7899	Intermediate Similarity	NPC317210
0.7899	Intermediate Similarity	NPC474271
0.7899	Intermediate Similarity	NPC472926
0.7891	Intermediate Similarity	NPC471855
0.7886	Intermediate Similarity	NPC102822
0.7886	Intermediate Similarity	NPC477046
0.7881	Intermediate Similarity	NPC469655

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC5989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1952
0.2-0.3	3682
0.3-0.4	2112
0.4-0.5	771
0.5-0.6	242
0.6-0.7	158
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7949	Intermediate Similarity	NPD6371	Approved
0.7815	Intermediate Similarity	NPD8297	Approved
0.7583	Intermediate Similarity	NPD6649	Approved
0.7583	Intermediate Similarity	NPD6650	Approved
0.7563	Intermediate Similarity	NPD6373	Approved
0.7563	Intermediate Similarity	NPD6372	Approved
0.752	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7479	Intermediate Similarity	NPD6881	Approved
0.7479	Intermediate Similarity	NPD6899	Approved
0.7459	Intermediate Similarity	NPD4632	Approved
0.7458	Intermediate Similarity	NPD6675	Approved
0.7458	Intermediate Similarity	NPD6402	Approved
0.7458	Intermediate Similarity	NPD5739	Approved
0.7458	Intermediate Similarity	NPD7128	Approved
0.7438	Intermediate Similarity	NPD8130	Phase 1
0.7419	Intermediate Similarity	NPD7115	Discovery
0.7417	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5344	Discontinued
0.7395	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5697	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.7355	Intermediate Similarity	NPD7102	Approved
0.7355	Intermediate Similarity	NPD7290	Approved
0.7355	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7320	Approved
0.7295	Intermediate Similarity	NPD6847	Approved
0.7295	Intermediate Similarity	NPD6617	Approved
0.7295	Intermediate Similarity	NPD6869	Approved
0.7287	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7252	Intermediate Similarity	NPD7736	Approved
0.725	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5701	Approved
0.7244	Intermediate Similarity	NPD6054	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7203	Intermediate Similarity	NPD5211	Phase 2
0.719	Intermediate Similarity	NPD6011	Approved
0.7188	Intermediate Similarity	NPD5983	Phase 2
0.7179	Intermediate Similarity	NPD7640	Approved
0.7179	Intermediate Similarity	NPD7639	Approved
0.7179	Intermediate Similarity	NPD6648	Approved
0.7176	Intermediate Similarity	NPD8293	Discontinued
0.7176	Intermediate Similarity	NPD7078	Approved
0.7167	Intermediate Similarity	NPD6008	Approved
0.7132	Intermediate Similarity	NPD6370	Approved
0.7109	Intermediate Similarity	NPD6059	Approved
0.7099	Intermediate Similarity	NPD7507	Approved
0.7099	Intermediate Similarity	NPD6336	Discontinued
0.7094	Intermediate Similarity	NPD4225	Approved
0.7094	Intermediate Similarity	NPD7638	Approved
0.7083	Intermediate Similarity	NPD5141	Approved
0.7077	Intermediate Similarity	NPD8328	Phase 3
0.7068	Intermediate Similarity	NPD7319	Approved
0.7054	Intermediate Similarity	NPD6015	Approved
0.7054	Intermediate Similarity	NPD6016	Approved
0.7049	Intermediate Similarity	NPD6686	Approved
0.7034	Intermediate Similarity	NPD4696	Approved
0.7034	Intermediate Similarity	NPD5285	Approved
0.7034	Intermediate Similarity	NPD5286	Approved
0.7031	Intermediate Similarity	NPD7516	Approved
0.7016	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4755	Approved
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD5988	Approved
0.6953	Remote Similarity	NPD7328	Approved
0.6953	Remote Similarity	NPD7327	Approved
0.6935	Remote Similarity	NPD4634	Approved
0.693	Remote Similarity	NPD6698	Approved
0.693	Remote Similarity	NPD46	Approved
0.6929	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD5225	Approved
0.6917	Remote Similarity	NPD5226	Approved
0.6917	Remote Similarity	NPD4633	Approved
0.6899	Remote Similarity	NPD7101	Approved
0.6899	Remote Similarity	NPD7100	Approved
0.6891	Remote Similarity	NPD4700	Approved
0.6864	Remote Similarity	NPD7902	Approved
0.686	Remote Similarity	NPD5175	Approved
0.686	Remote Similarity	NPD5174	Approved
0.6855	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5695	Phase 3
0.6833	Remote Similarity	NPD5223	Approved
0.6825	Remote Similarity	NPD6053	Discontinued
0.6822	Remote Similarity	NPD6335	Approved
0.681	Remote Similarity	NPD6399	Phase 3
0.6807	Remote Similarity	NPD5696	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.6794	Remote Similarity	NPD8296	Approved
0.6794	Remote Similarity	NPD8380	Approved
0.6794	Remote Similarity	NPD8379	Approved
0.6794	Remote Similarity	NPD8033	Approved
0.6794	Remote Similarity	NPD8378	Approved
0.6794	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD1696	Phase 3
0.6774	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4729	Approved
0.6752	Remote Similarity	NPD5282	Discontinued
0.6752	Remote Similarity	NPD7748	Approved
0.6748	Remote Similarity	NPD4768	Approved
0.6748	Remote Similarity	NPD4767	Approved
0.6744	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7983	Approved
0.6718	Remote Similarity	NPD8377	Approved
0.6718	Remote Similarity	NPD8294	Approved
0.6695	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6412	Phase 2
0.6692	Remote Similarity	NPD6314	Approved
0.6692	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD6909	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8133	Approved
0.664	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD4697	Phase 3
0.6638	Remote Similarity	NPD7838	Discovery
0.6618	Remote Similarity	NPD6033	Approved
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7900	Approved
0.6594	Remote Similarity	NPD7260	Phase 2
0.6585	Remote Similarity	NPD4754	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6581	Remote Similarity	NPD7515	Phase 2
0.6581	Remote Similarity	NPD6079	Approved
0.6557	Remote Similarity	NPD1700	Approved
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD1695	Approved
0.6541	Remote Similarity	NPD8517	Approved
0.6541	Remote Similarity	NPD8513	Phase 3
0.6541	Remote Similarity	NPD8515	Approved
0.6541	Remote Similarity	NPD7503	Approved
0.6541	Remote Similarity	NPD8516	Approved
0.6538	Remote Similarity	NPD6868	Approved
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5778	Approved
0.6525	Remote Similarity	NPD5779	Approved
0.6525	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD5785	Approved
0.6484	Remote Similarity	NPD5215	Approved
0.6484	Remote Similarity	NPD5216	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6441	Remote Similarity	NPD7637	Suspended
0.6441	Remote Similarity	NPD8035	Phase 2
0.6441	Remote Similarity	NPD8034	Phase 2
0.6435	Remote Similarity	NPD3618	Phase 1
0.641	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD6673	Approved
0.641	Remote Similarity	NPD6904	Approved
0.6406	Remote Similarity	NPD5169	Approved
0.6406	Remote Similarity	NPD5135	Approved
0.6406	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7524	Approved
0.6357	Remote Similarity	NPD5127	Approved
0.6348	Remote Similarity	NPD1694	Approved
0.6348	Remote Similarity	NPD5363	Approved
0.6333	Remote Similarity	NPD6001	Approved
0.6316	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD6110	Phase 1
0.6316	Remote Similarity	NPD5362	Discontinued
0.6312	Remote Similarity	NPD6845	Suspended
0.6304	Remote Similarity	NPD8074	Phase 3
0.6303	Remote Similarity	NPD5284	Approved
0.6303	Remote Similarity	NPD5281	Approved
0.6303	Remote Similarity	NPD5693	Phase 1
0.6303	Remote Similarity	NPD6050	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6293	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4786	Approved
0.6239	Remote Similarity	NPD3573	Approved
0.6228	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5692	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data