NPASS Compound

Structure

CID4309 OpenBabel06191715322D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.7278 -0.3469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1908 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4716 -4.3471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4555 -1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9622 -0.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0249 -1.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8732 1.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 -0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8232 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1175 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6461 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6475 -2.8517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8240 -2.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8229 0.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 1.9005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8241 1.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6478 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7891 -0.1979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3248 -3.8538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1172 0.4743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6464 -0.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4704 -2.3759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4711 0.4748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4716 2.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4699 -1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8235 -1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8238 0.4753 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 -2.4714 1.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1786 -4.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5678 2.6697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1781 3.0115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3243 -2.8682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 18 1 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 19 1 6 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 30 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 32 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	6.483
LogD:	5.487
LogS:	-5.334
# Rotatable Bonds:	4
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.725
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.36
MDCK Permeability:	4.451879067346454e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	89.00924682617188%
Volume Distribution (VD):	0.779
Pgp-substrate:	2.8571817874908447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.555
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	2.102
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.638
Skin Sensitization:	0.289
Carcinogencity:	0.007
Eye Corrosion:	0.852
Eye Irritation:	0.593
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC4309

Natural Product ID:	NPC4309
*Common Name:**	3-Acetylbetulinic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	(3-O-Acetyl)Betulinic Acid; 3-Acetylbetulinic Acid; 3-O-Acetyl Betulinic Acid; Betulinic Acid 3-O-Acetate
Standard InCHIKey:	ACWNTJJUZAIOLW-BWXYOZBYSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)22(26(21)32)9-10-24-29(6)14-13-25(36-20(3)33)28(4,5)23(29)12-15-31(24,30)8/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23-,24+,25-,26+,29-,30+,31+,32-/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL312687
PubChem CID:	10300534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1021/np50040a042]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	eggs	Pacific	n.a.	PMID[10654418]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	Eggs	n.a.	n.a.	PMID[10654418]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	Azorean	n.a.	PMID[20227875]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2832544]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9433811]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO241	Teucrium cossonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5809	Xanthoparmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3528	Cinnamomum pedunculatum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1244	Trimusculus conica	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1977	Arum montanum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6951	Dictyota spinulosa	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4050	Boronia lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO518	Mercurialis leiocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3023	Achillea pratensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1659	Primula denticulata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4125	Corydalis crystallina	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1814	Euphorbia cattimandoo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4204	Ochradenus baccatus	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3456	Eucalyptus campanulata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4411	Plantago ovata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7161	Capparis angulata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7640	Klaseopsis chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO798	Chloranthus holostegius	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6345	Podocarpus sellowii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6523	Streptococcus pneumoniae	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16714	Campanula pendula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2339	Turnera ulmifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3913	Alcea nudiflora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4350	Chlorella pyrenoidosa	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6107	Acacia lemmoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5739	Rubus foliolosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO586	Lomandra hastilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10450	Clerodendrum infortunatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5518	Thuja dolabrata	Species	Cupressaceae	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	14
GI50	4
IC50	22
Others	18

Activity Type	# Activity
Cell Line	37
Individual Protein	2
NON-MOLECULAR	3
Organism	2
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	>	11300.0	nM	PMID[448181]
NPT387	Cell Line	M14	Homo sapiens	GI50	>	6400.0	nM	PMID[448181]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	>	3900.0	nM	PMID[448181]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	>	4500.0	nM	PMID[448181]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	>	7200000.0	nM	PMID[448181]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	>	6900000.0	nM	PMID[448181]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	18000.0	nM	PMID[448182]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	20000.0	nM	PMID[448182]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[448183]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[448183]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	17000.0	nM	PMID[448184]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	19000.0	nM	PMID[448184]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	18000.0	nM	PMID[448184]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	24000.0	nM	PMID[448184]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	200000.0	nM	PMID[448184]
NPT759	Cell Line	H9	Homo sapiens	IC50	=	20000.0	nM	PMID[448185]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	10720.0	nM	PMID[448186]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6730.0	nM	PMID[448186]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	18990.0	nM	PMID[448186]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	16140.0	nM	PMID[448186]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11060.0	nM	PMID[448186]
NPT763	Cell Line	SW-1736	Homo sapiens	IC50	=	7300.0	nM	PMID[448186]
NPT179	Cell Line	A2780	Homo sapiens	EC50	=	18300.0	nM	PMID[448187]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	6200.0	nM	PMID[448187]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	11000.0	nM	PMID[448187]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	400000.0	nM	PMID[448188]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	400000.0	nM	PMID[448188]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6700.0	nM	PMID[448189]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9600.0	nM	PMID[448189]
NPT1083	Cell Line	A-375	Homo sapiens	EC50	=	19200.0	nM	PMID[448190]
NPT139	Cell Line	HT-29	Homo sapiens	EC50	=	21300.0	nM	PMID[448190]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	11000.0	nM	PMID[448190]
NPT179	Cell Line	A2780	Homo sapiens	EC50	=	18300.0	nM	PMID[448190]
NPT1216	Cell Line	FaDu	Homo sapiens	EC50	=	7200.0	nM	PMID[448190]
NPT886	Cell Line	NIH3T3	Mus musculus	EC50	>	30000.0	nM	PMID[448190]
NPT27	Others	Unspecified		IC50	=	57000.0	nM	PMID[448182]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[448183]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[448183]
NPT2	Others	Unspecified		Activity	=	55.1	%	PMID[448183]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	25000.0	nM	PMID[448185]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	0.8	n.a.	PMID[448185]
NPT760	Individual Protein	Protein kinase C beta	Homo sapiens	IC50	>	150000.0	nM	PMID[448185]
NPT761	Individual Protein	Protein kinase C epsilon	Homo sapiens	IC50	>	150000.0	nM	PMID[448185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4650.0	nM	PMID[448186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11840.0	nM	PMID[448186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4500.0	nM	PMID[448187]
NPT27	Others	Unspecified		EC50	>	30000.0	nM	PMID[448187]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	65500.0	nM	PMID[448188]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	6.11	n.a.	PMID[448188]
NPT2	Others	Unspecified		Ratio EC50	=	1.6	n.a.	PMID[448190]
NPT2	Others	Unspecified		Ratio EC50	=	1.4	n.a.	PMID[448190]
NPT2	Others	Unspecified		Ratio EC50	=	2.7	n.a.	PMID[448190]
NPT2	Others	Unspecified		Ratio EC50	=	4.2	n.a.	PMID[448190]

☑ 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 NPC4309 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	194
0.1-0.2	1616
0.2-0.3	6323
0.3-0.4	15734
0.4-0.5	6238
0.5-0.6	4915
0.6-0.7	4687
0.7-0.8	2540
0.8-0.85	355
0.85-0.9	53
0.9-0.95	28
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9647	High Similarity	NPC160506
0.9647	High Similarity	NPC471901
0.9639	High Similarity	NPC33768
0.9634	High Similarity	NPC98270
0.9535	High Similarity	NPC287118
0.9535	High Similarity	NPC471902
0.9535	High Similarity	NPC473690
0.9518	High Similarity	NPC12774
0.9518	High Similarity	NPC2783
0.9512	High Similarity	NPC475509
0.9419	High Similarity	NPC475416
0.9405	High Similarity	NPC264005
0.9405	High Similarity	NPC269360
0.9398	High Similarity	NPC294438
0.9398	High Similarity	NPC264317
0.939	High Similarity	NPC471037
0.9294	High Similarity	NPC474719
0.9294	High Similarity	NPC16377
0.9186	High Similarity	NPC271974
0.9186	High Similarity	NPC220498
0.9186	High Similarity	NPC247312
0.9186	High Similarity	NPC213832
0.9186	High Similarity	NPC57954
0.9157	High Similarity	NPC5280
0.9091	High Similarity	NPC475061
0.908	High Similarity	NPC471896
0.908	High Similarity	NPC169933
0.907	High Similarity	NPC471900
0.9059	High Similarity	NPC168231
0.9024	High Similarity	NPC261616
0.9024	High Similarity	NPC304194
0.8989	High Similarity	NPC303863
0.8966	High Similarity	NPC474889
0.8929	High Similarity	NPC475726
0.8929	High Similarity	NPC472743
0.8902	High Similarity	NPC305835
0.8889	High Similarity	NPC279974
0.8876	High Similarity	NPC244356
0.8876	High Similarity	NPC291373
0.8876	High Similarity	NPC224060
0.8864	High Similarity	NPC148414
0.8864	High Similarity	NPC111585
0.8864	High Similarity	NPC120840
0.8864	High Similarity	NPC175628
0.8864	High Similarity	NPC113989
0.8824	High Similarity	NPC264665
0.8824	High Similarity	NPC74595
0.8824	High Similarity	NPC475745
0.8824	High Similarity	NPC474482
0.8795	High Similarity	NPC206735
0.8791	High Similarity	NPC327788
0.8778	High Similarity	NPC277399
0.8764	High Similarity	NPC470590
0.8764	High Similarity	NPC285184
0.8764	High Similarity	NPC77099
0.8764	High Similarity	NPC60755
0.8764	High Similarity	NPC26888
0.875	High Similarity	NPC30522
0.8721	High Similarity	NPC201655
0.8721	High Similarity	NPC292553
0.8706	High Similarity	NPC473742
0.8681	High Similarity	NPC205173
0.8675	High Similarity	NPC192744
0.8667	High Similarity	NPC86368
0.8667	High Similarity	NPC294263
0.8659	High Similarity	NPC68828
0.8652	High Similarity	NPC474728
0.8636	High Similarity	NPC146937
0.8621	High Similarity	NPC472505
0.8621	High Similarity	NPC472738
0.8621	High Similarity	NPC269396
0.8621	High Similarity	NPC187545
0.8621	High Similarity	NPC98236
0.8605	High Similarity	NPC474233
0.8602	High Similarity	NPC119036
0.8602	High Similarity	NPC472028
0.8588	High Similarity	NPC61107
0.8588	High Similarity	NPC289486
0.8571	High Similarity	NPC78580
0.8571	High Similarity	NPC23621
0.8571	High Similarity	NPC296164
0.8571	High Similarity	NPC47853
0.8571	High Similarity	NPC184006
0.8571	High Similarity	NPC159410
0.8571	High Similarity	NPC74751
0.8554	High Similarity	NPC63020
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC475921
0.8537	High Similarity	NPC246445
0.8523	High Similarity	NPC142361
0.8523	High Similarity	NPC4643
0.8523	High Similarity	NPC57469
0.8523	High Similarity	NPC162107
0.8523	High Similarity	NPC46912
0.8523	High Similarity	NPC134197
0.8523	High Similarity	NPC474684
0.8511	High Similarity	NPC94906
0.8495	Intermediate Similarity	NPC253586
0.8488	Intermediate Similarity	NPC245866
0.8478	Intermediate Similarity	NPC98639
0.8478	Intermediate Similarity	NPC195715
0.8478	Intermediate Similarity	NPC69548
0.8478	Intermediate Similarity	NPC184848
0.8478	Intermediate Similarity	NPC474727
0.8478	Intermediate Similarity	NPC23241
0.8478	Intermediate Similarity	NPC210214
0.8478	Intermediate Similarity	NPC470229
0.8462	Intermediate Similarity	NPC49776
0.8462	Intermediate Similarity	NPC470224
0.8462	Intermediate Similarity	NPC474436
0.8462	Intermediate Similarity	NPC63118
0.8452	Intermediate Similarity	NPC47808
0.8452	Intermediate Similarity	NPC201459
0.8434	Intermediate Similarity	NPC66105
0.8434	Intermediate Similarity	NPC143133
0.8434	Intermediate Similarity	NPC298168
0.8427	Intermediate Similarity	NPC246708
0.8427	Intermediate Similarity	NPC52169
0.8427	Intermediate Similarity	NPC182797
0.8427	Intermediate Similarity	NPC255176
0.8427	Intermediate Similarity	NPC472739
0.8427	Intermediate Similarity	NPC242864
0.8427	Intermediate Similarity	NPC40552
0.8421	Intermediate Similarity	NPC75941
0.8409	Intermediate Similarity	NPC91525
0.8409	Intermediate Similarity	NPC9892
0.8409	Intermediate Similarity	NPC329943
0.8409	Intermediate Similarity	NPC325594
0.8409	Intermediate Similarity	NPC471042
0.8409	Intermediate Similarity	NPC55309
0.8409	Intermediate Similarity	NPC70661
0.8409	Intermediate Similarity	NPC10005
0.8409	Intermediate Similarity	NPC80590
0.8409	Intermediate Similarity	NPC28252
0.8391	Intermediate Similarity	NPC263974
0.8391	Intermediate Similarity	NPC299963
0.8391	Intermediate Similarity	NPC239362
0.8387	Intermediate Similarity	NPC200054
0.8387	Intermediate Similarity	NPC329910
0.8387	Intermediate Similarity	NPC327179
0.8387	Intermediate Similarity	NPC230151
0.8387	Intermediate Similarity	NPC29410
0.8387	Intermediate Similarity	NPC120708
0.8372	Intermediate Similarity	NPC472504
0.837	Intermediate Similarity	NPC475118
0.8352	Intermediate Similarity	NPC250753
0.8352	Intermediate Similarity	NPC189520
0.8333	Intermediate Similarity	NPC243594
0.8333	Intermediate Similarity	NPC31031
0.8333	Intermediate Similarity	NPC59263
0.8333	Intermediate Similarity	NPC293048
0.8333	Intermediate Similarity	NPC124544
0.8333	Intermediate Similarity	NPC198664
0.8333	Intermediate Similarity	NPC127689
0.8333	Intermediate Similarity	NPC130520
0.8333	Intermediate Similarity	NPC121798
0.8333	Intermediate Similarity	NPC263393
0.8333	Intermediate Similarity	NPC61543
0.8333	Intermediate Similarity	NPC225585
0.8333	Intermediate Similarity	NPC25906
0.8333	Intermediate Similarity	NPC143232
0.8333	Intermediate Similarity	NPC234346
0.8333	Intermediate Similarity	NPC64872
0.8333	Intermediate Similarity	NPC270768
0.8333	Intermediate Similarity	NPC471043
0.8333	Intermediate Similarity	NPC470588
0.8333	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC290972
0.8333	Intermediate Similarity	NPC269267
0.8333	Intermediate Similarity	NPC274330
0.8333	Intermediate Similarity	NPC475049
0.8316	Intermediate Similarity	NPC108371
0.8315	Intermediate Similarity	NPC187376
0.8315	Intermediate Similarity	NPC102683
0.8315	Intermediate Similarity	NPC142415
0.8315	Intermediate Similarity	NPC51700
0.8315	Intermediate Similarity	NPC242468
0.8315	Intermediate Similarity	NPC171203
0.8315	Intermediate Similarity	NPC233836
0.8315	Intermediate Similarity	NPC18064
0.8315	Intermediate Similarity	NPC159046
0.8315	Intermediate Similarity	NPC307426
0.8315	Intermediate Similarity	NPC68160
0.8315	Intermediate Similarity	NPC293564
0.8315	Intermediate Similarity	NPC130577
0.8315	Intermediate Similarity	NPC98442
0.8315	Intermediate Similarity	NPC88716
0.8313	Intermediate Similarity	NPC4209
0.8298	Intermediate Similarity	NPC26413
0.8298	Intermediate Similarity	NPC476878
0.8298	Intermediate Similarity	NPC476879
0.8298	Intermediate Similarity	NPC158347
0.8295	Intermediate Similarity	NPC474971
0.8295	Intermediate Similarity	NPC76518
0.8283	Intermediate Similarity	NPC88744
0.828	Intermediate Similarity	NPC288906
0.828	Intermediate Similarity	NPC470232
0.828	Intermediate Similarity	NPC84383
0.828	Intermediate Similarity	NPC263135
0.828	Intermediate Similarity	NPC266431

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 NPC4309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1969
0.2-0.3	4118
0.3-0.4	1958
0.4-0.5	477
0.5-0.6	166
0.6-0.7	187
0.7-0.8	88
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9647	High Similarity	NPD8035	Phase 2
0.9647	High Similarity	NPD8034	Phase 2
0.9398	High Similarity	NPD7520	Clinical (unspecified phase)
0.8571	High Similarity	NPD7748	Approved
0.8313	Intermediate Similarity	NPD6117	Approved
0.8298	Intermediate Similarity	NPD7902	Approved
0.8261	Intermediate Similarity	NPD6399	Phase 3
0.8214	Intermediate Similarity	NPD6116	Phase 1
0.8152	Intermediate Similarity	NPD7515	Phase 2
0.8118	Intermediate Similarity	NPD6114	Approved
0.8118	Intermediate Similarity	NPD6115	Approved
0.8118	Intermediate Similarity	NPD6118	Approved
0.8118	Intermediate Similarity	NPD6697	Approved
0.8072	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7900	Approved
0.7979	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4786	Approved
0.7755	Intermediate Similarity	NPD7640	Approved
0.7755	Intermediate Similarity	NPD7639	Approved
0.7742	Intermediate Similarity	NPD5328	Approved
0.7723	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD7128	Approved
0.7723	Intermediate Similarity	NPD6402	Approved
0.7723	Intermediate Similarity	NPD5739	Approved
0.7667	Intermediate Similarity	NPD4788	Approved
0.7634	Intermediate Similarity	NPD6672	Approved
0.7634	Intermediate Similarity	NPD5737	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD3618	Phase 1
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD6079	Approved
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7573	Intermediate Similarity	NPD7320	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7528	Intermediate Similarity	NPD7525	Registered
0.7524	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD5697	Approved
0.7453	Intermediate Similarity	NPD8297	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD6883	Approved
0.7412	Intermediate Similarity	NPD5777	Approved
0.7412	Intermediate Similarity	NPD6081	Approved
0.7404	Intermediate Similarity	NPD6011	Approved
0.7383	Intermediate Similarity	NPD8133	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6650	Approved
0.7358	Intermediate Similarity	NPD6649	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7356	Intermediate Similarity	NPD3702	Approved
0.7347	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5695	Phase 3
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD6012	Approved
0.732	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD5696	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD5222	Approved
0.7273	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5360	Phase 3
0.7262	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7632	Discontinued
0.7234	Intermediate Similarity	NPD6098	Approved
0.7229	Intermediate Similarity	NPD4224	Phase 2
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7204	Intermediate Similarity	NPD3665	Phase 1
0.7204	Intermediate Similarity	NPD3668	Phase 3
0.7204	Intermediate Similarity	NPD3133	Approved
0.7204	Intermediate Similarity	NPD3666	Approved
0.72	Intermediate Similarity	NPD5173	Approved
0.72	Intermediate Similarity	NPD4755	Approved
0.7188	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6673	Approved
0.7188	Intermediate Similarity	NPD6904	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7159	Intermediate Similarity	NPD3703	Phase 2
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.7091	Intermediate Similarity	NPD6868	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD4696	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD5286	Approved
0.7048	Intermediate Similarity	NPD6008	Approved
0.701	Intermediate Similarity	NPD4753	Phase 2
0.699	Remote Similarity	NPD5223	Approved
0.6989	Remote Similarity	NPD4223	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6979	Remote Similarity	NPD3573	Approved
0.6977	Remote Similarity	NPD3698	Phase 2
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD6942	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6947	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD6274	Approved
0.6923	Remote Similarity	NPD5211	Phase 2
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6907	Remote Similarity	NPD5208	Approved
0.6905	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.69	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.6869	Remote Similarity	NPD5284	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6864	Remote Similarity	NPD7736	Approved
0.6857	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD5174	Approved
0.6857	Remote Similarity	NPD4754	Approved
0.6852	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4197	Approved
0.6838	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6051	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD4758	Discontinued
0.6814	Remote Similarity	NPD6314	Approved
0.6814	Remote Similarity	NPD6313	Approved
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5141	Approved
0.6783	Remote Similarity	NPD6909	Approved
0.6783	Remote Similarity	NPD6908	Approved
0.6782	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5692	Phase 3
0.6739	Remote Similarity	NPD3671	Phase 1
0.6739	Remote Similarity	NPD3617	Approved
0.6739	Remote Similarity	NPD5364	Discontinued
0.6739	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8418	Phase 2
0.6729	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD4768	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4693	Phase 3
0.6701	Remote Similarity	NPD4138	Approved
0.6701	Remote Similarity	NPD4688	Approved
0.6701	Remote Similarity	NPD4690	Approved
0.6701	Remote Similarity	NPD4689	Approved
0.6701	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD5694	Approved
0.67	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD8293	Discontinued
0.6638	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4225	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6606	Remote Similarity	NPD5168	Approved
0.6606	Remote Similarity	NPD4730	Approved
0.6606	Remote Similarity	NPD4729	Approved
0.6606	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5128	Approved
0.66	Remote Similarity	NPD5207	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6555	Remote Similarity	NPD6336	Discontinued
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6552	Remote Similarity	NPD8294	Approved

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