NPASS Compound

Structure

CID278175 OpenBabel06191716082D 38 41 0 0 0 0 0 0 0 0999 V2000 -5.9178 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4541 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8216 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3335 -0.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6087 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7632 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7632 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6087 2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6087 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 2.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 24 2 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 31 2 0 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 24 1 0 0 0 0 19 27 2 0 0 0 0 20 26 1 0 0 0 0 20 28 2 0 0 0 0 21 23 1 0 0 0 0 21 32 2 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 23 29 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.18
Volume:	529.258
LogP:	6.153
LogD:	2.32
LogS:	-3.639
# Rotatable Bonds:	6
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	3.314
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.411
MDCK Permeability:	2.1189995095483027e-05
Pgp-inhibitor:	0.565
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.121
20% Bioavailability (F20%):	0.242
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	103.35675811767578%
Volume Distribution (VD):	0.199
Pgp-substrate:	0.804043173789978%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.278
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.317
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	3.5
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.739
Skin Sensitization:	0.957
Carcinogencity:	0.367
Eye Corrosion:	0.003
Eye Irritation:	0.855
Respiratory Toxicity:	0.201

Download Data

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

Natural Product: NPC278175

Natural Product ID:	NPC278175
*Common Name:**	(Z)-1-[6-[(3-Acetyl-2,4,6-Trihydroxy-5-Methylphenyl)Methyl]-5,7-Dihydroxy-2,2-Dimethylchromen-8-Yl]-3-Phenylprop-2-En-1-One
IUPAC Name:	(Z)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	DEZFNHCVIZBHBI-KHPPLWFESA-N
Standard InCHI:	InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10-
SMILES:	Cc1c(c(Cc2c(c3C=CC(C)(C)Oc3c(C(=O)/C=Cc3ccccc3)c2O)O)c(c(C(=O)C)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1330502
PubChem CID:	6603986
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)93394-0]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10814365]
NPO29801	Mallotus philippinensis	Species	Salangidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO25967	Mallotus philippensis	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12499591]
NPO25967	Mallotus philippensis	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15516755]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26476665]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26483136]
NPO25967	Mallotus philippensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31318550]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322358]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29780	Cassia mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29801	Mallotus philippinensis	Species	Salangidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30848	Millettia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5367	Derris trifoliata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9035	Verbascum thapsus	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30811	Cassia angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29240	Callerya reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5367	Derris trifoliata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25967	Mallotus philippensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9035	Verbascum thapsus	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29780	Cassia mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30179	Cassia occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5367	Derris trifoliata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30811	Cassia angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9035	Verbascum thapsus	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29240	Callerya reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6470	Pachyrhizus erosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25967	Mallotus philippensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22654	Millettia pachycarpa	Species	Fabaceae	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
AC50	2
Potency	39

Activity Type	# Activity
Individual Protein	35
Others	4
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	=	794.3	nM	PMID[536636]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[536636]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	19952.6	nM	PMID[536636]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	14125.4	nM	PMID[536636]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	10000.0	nM	PMID[536636]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	1995.3	nM	PMID[536637]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[536636]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	44668.4	nM	PMID[536636]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	39810.7	nM	PMID[536636]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	15848.9	nM	PMID[536636]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	10000.0	nM	PMID[536637]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	31622.8	nM	PMID[536636]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[536636]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	39810.7	nM	PMID[536636]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PMID[536636]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	1000.0	nM	PMID[536636]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	12589.3	nM	PMID[536637]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	6309.6	nM	PMID[536636]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	631.0	nM	PMID[536637]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[536636]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	1000.0	nM	PMID[536636]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	12589.25	nM	PMID[536636]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	31622.78	nM	PMID[536636]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[536636]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[536636]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[536636]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	13335.9	nM	PMID[536636]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	22387.2	nM	PMID[536636]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	39810.7	nM	PMID[536636]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	31622.8	nM	PMID[536636]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	3162.3	nM	PMID[536636]
NPT96	Individual Protein	Thrombopoietin	Homo sapiens	Potency	=	2511.9	nM	PMID[536636]
NPT2	Others	Unspecified		Potency	=	2818.4	nM	PMID[536636]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[536636]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[536636]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[536636]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[536636]

☑ 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 NPC278175 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	390
0.1-0.2	1629
0.2-0.3	4128
0.3-0.4	11002
0.4-0.5	7344
0.5-0.6	3912
0.6-0.7	5996
0.7-0.8	4852
0.8-0.85	2032
0.85-0.9	963
0.9-0.95	426
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257236
0.9643	High Similarity	NPC38219
0.964	High Similarity	NPC205006
0.964	High Similarity	NPC14871
0.964	High Similarity	NPC147688
0.964	High Similarity	NPC156590
0.964	High Similarity	NPC64908
0.964	High Similarity	NPC118840
0.9571	High Similarity	NPC11561
0.9571	High Similarity	NPC299080
0.9571	High Similarity	NPC78803
0.9571	High Similarity	NPC217083
0.9571	High Similarity	NPC226636
0.9571	High Similarity	NPC59739
0.9571	High Similarity	NPC62840
0.9571	High Similarity	NPC214236
0.9571	High Similarity	NPC293852
0.9568	High Similarity	NPC235239
0.9568	High Similarity	NPC261227
0.9568	High Similarity	NPC270883
0.9568	High Similarity	NPC172986
0.9568	High Similarity	NPC305355
0.9568	High Similarity	NPC475680
0.9514	High Similarity	NPC151973
0.9507	High Similarity	NPC228779
0.9504	High Similarity	NPC219915
0.95	High Similarity	NPC103362
0.95	High Similarity	NPC110969
0.9496	High Similarity	NPC220062
0.9496	High Similarity	NPC96565
0.9496	High Similarity	NPC216978
0.9496	High Similarity	NPC301217
0.9496	High Similarity	NPC303633
0.9496	High Similarity	NPC217186
0.9496	High Similarity	NPC55018
0.9496	High Similarity	NPC53181
0.9441	High Similarity	NPC23728
0.9441	High Similarity	NPC24673
0.9441	High Similarity	NPC201731
0.9441	High Similarity	NPC97716
0.9441	High Similarity	NPC110303
0.9441	High Similarity	NPC180477
0.9441	High Similarity	NPC104406
0.9441	High Similarity	NPC237635
0.9441	High Similarity	NPC79469
0.9437	High Similarity	NPC469953
0.9437	High Similarity	NPC234629
0.9437	High Similarity	NPC311741
0.9433	High Similarity	NPC144499
0.9429	High Similarity	NPC241100
0.9429	High Similarity	NPC150522
0.9429	High Similarity	NPC69769
0.9429	High Similarity	NPC159275
0.9424	High Similarity	NPC272844
0.9424	High Similarity	NPC248995
0.9424	High Similarity	NPC201395
0.9424	High Similarity	NPC254168
0.9375	High Similarity	NPC266572
0.9375	High Similarity	NPC132592
0.9375	High Similarity	NPC160821
0.9375	High Similarity	NPC6511
0.9371	High Similarity	NPC470131
0.9371	High Similarity	NPC57470
0.9371	High Similarity	NPC312973
0.9371	High Similarity	NPC88964
0.9371	High Similarity	NPC470647
0.9371	High Similarity	NPC142405
0.9371	High Similarity	NPC470134
0.9371	High Similarity	NPC54577
0.9371	High Similarity	NPC475052
0.9371	High Similarity	NPC83357
0.9371	High Similarity	NPC473078
0.9371	High Similarity	NPC20488
0.9371	High Similarity	NPC246948
0.9371	High Similarity	NPC301276
0.9371	High Similarity	NPC111786
0.9371	High Similarity	NPC220418
0.9371	High Similarity	NPC109183
0.9371	High Similarity	NPC470133
0.9371	High Similarity	NPC195621
0.9371	High Similarity	NPC267375
0.9371	High Similarity	NPC176229
0.9371	High Similarity	NPC214774
0.9371	High Similarity	NPC67805
0.9371	High Similarity	NPC470132
0.9366	High Similarity	NPC18585
0.9366	High Similarity	NPC106985
0.9366	High Similarity	NPC166138
0.9362	High Similarity	NPC282300
0.9357	High Similarity	NPC18260
0.9357	High Similarity	NPC78913
0.9357	High Similarity	NPC240305
0.931	High Similarity	NPC291746
0.931	High Similarity	NPC288840
0.931	High Similarity	NPC37208
0.931	High Similarity	NPC221868
0.9306	High Similarity	NPC297886
0.9306	High Similarity	NPC140120
0.9306	High Similarity	NPC249942
0.9306	High Similarity	NPC14001
0.9306	High Similarity	NPC296998
0.9306	High Similarity	NPC283234
0.9306	High Similarity	NPC166757
0.9306	High Similarity	NPC473077
0.9301	High Similarity	NPC319752
0.9301	High Similarity	NPC470135
0.9301	High Similarity	NPC39045
0.9301	High Similarity	NPC209040
0.9301	High Similarity	NPC470136
0.9296	High Similarity	NPC200694
0.9296	High Similarity	NPC36181
0.9286	High Similarity	NPC243528
0.9286	High Similarity	NPC470669
0.9286	High Similarity	NPC470668
0.9286	High Similarity	NPC251681
0.9281	High Similarity	NPC13408
0.9247	High Similarity	NPC188403
0.9241	High Similarity	NPC244407
0.9241	High Similarity	NPC272194
0.9241	High Similarity	NPC469933
0.9241	High Similarity	NPC296869
0.9241	High Similarity	NPC208303
0.9241	High Similarity	NPC321623
0.9241	High Similarity	NPC161191
0.9241	High Similarity	NPC161864
0.9241	High Similarity	NPC189087
0.9236	High Similarity	NPC474161
0.9236	High Similarity	NPC477955
0.9236	High Similarity	NPC124729
0.9236	High Similarity	NPC476088
0.9231	High Similarity	NPC112791
0.9231	High Similarity	NPC164980
0.9231	High Similarity	NPC9117
0.9231	High Similarity	NPC87609
0.9231	High Similarity	NPC196459
0.9231	High Similarity	NPC188632
0.9231	High Similarity	NPC190637
0.9231	High Similarity	NPC310130
0.9231	High Similarity	NPC212932
0.9231	High Similarity	NPC68104
0.9231	High Similarity	NPC91560
0.9231	High Similarity	NPC11700
0.9231	High Similarity	NPC293053
0.9231	High Similarity	NPC75049
0.9231	High Similarity	NPC478086
0.9231	High Similarity	NPC221432
0.9231	High Similarity	NPC24821
0.9231	High Similarity	NPC39329
0.9231	High Similarity	NPC94794
0.9231	High Similarity	NPC169591
0.9231	High Similarity	NPC175504
0.9231	High Similarity	NPC214166
0.9231	High Similarity	NPC143896
0.9231	High Similarity	NPC470296
0.9231	High Similarity	NPC149026
0.9231	High Similarity	NPC257097
0.9231	High Similarity	NPC316816
0.9231	High Similarity	NPC150408
0.9225	High Similarity	NPC3188
0.9225	High Similarity	NPC110038
0.9225	High Similarity	NPC26238
0.9225	High Similarity	NPC248372
0.922	High Similarity	NPC283429
0.922	High Similarity	NPC23257
0.9214	High Similarity	NPC228661
0.9214	High Similarity	NPC317119
0.9214	High Similarity	NPC250266
0.9214	High Similarity	NPC157855
0.9214	High Similarity	NPC266597
0.9209	High Similarity	NPC151113
0.9209	High Similarity	NPC156092
0.9209	High Similarity	NPC101752
0.9195	High Similarity	NPC56049
0.9195	High Similarity	NPC54830
0.9189	High Similarity	NPC71061
0.9189	High Similarity	NPC303485
0.9189	High Similarity	NPC290830
0.9189	High Similarity	NPC72425
0.9189	High Similarity	NPC194593
0.9184	High Similarity	NPC111112
0.9184	High Similarity	NPC67322
0.9184	High Similarity	NPC305965
0.9184	High Similarity	NPC138299
0.9184	High Similarity	NPC222713
0.9178	High Similarity	NPC164205
0.9178	High Similarity	NPC10027
0.9178	High Similarity	NPC5173
0.9178	High Similarity	NPC469932
0.9178	High Similarity	NPC104236
0.9178	High Similarity	NPC3642
0.9178	High Similarity	NPC65775
0.9167	High Similarity	NPC178627
0.9167	High Similarity	NPC197252
0.9167	High Similarity	NPC1886
0.9167	High Similarity	NPC326500
0.9167	High Similarity	NPC469935
0.9167	High Similarity	NPC473015
0.9167	High Similarity	NPC236766
0.9167	High Similarity	NPC273538
0.9167	High Similarity	NPC196137

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 NPC278175 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	966
0.2-0.3	1467
0.3-0.4	2685
0.4-0.5	1937
0.5-0.6	1181
0.6-0.7	362
0.7-0.8	147
0.8-0.85	33
0.85-0.9	16
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7410	Clinical (unspecified phase)
0.9184	High Similarity	NPD7411	Suspended
0.9167	High Similarity	NPD4378	Clinical (unspecified phase)
0.9	High Similarity	NPD8443	Clinical (unspecified phase)
0.8881	High Similarity	NPD1549	Phase 2
0.8859	High Similarity	NPD4380	Phase 2
0.8811	High Similarity	NPD1550	Clinical (unspecified phase)
0.8811	High Similarity	NPD1552	Clinical (unspecified phase)
0.8803	High Similarity	NPD1510	Phase 2
0.8786	High Similarity	NPD1240	Approved
0.8741	High Similarity	NPD2796	Approved
0.8662	High Similarity	NPD7852	Clinical (unspecified phase)
0.8662	High Similarity	NPD1607	Approved
0.8636	High Similarity	NPD7075	Discontinued
0.8618	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD7768	Phase 2
0.8562	High Similarity	NPD7421	Clinical (unspecified phase)
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD3749	Approved
0.8516	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD3750	Approved
0.8471	Intermediate Similarity	NPD6959	Discontinued
0.8456	Intermediate Similarity	NPD1511	Approved
0.8442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6166	Phase 2
0.8311	Intermediate Similarity	NPD2800	Approved
0.8276	Intermediate Similarity	NPD6651	Approved
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1934	Approved
0.8188	Intermediate Similarity	NPD1243	Approved
0.817	Intermediate Similarity	NPD5403	Approved
0.8163	Intermediate Similarity	NPD3748	Approved
0.8129	Intermediate Similarity	NPD6599	Discontinued
0.8125	Intermediate Similarity	NPD2313	Discontinued
0.8101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8054	Intermediate Similarity	NPD2344	Approved
0.8041	Intermediate Similarity	NPD2799	Discontinued
0.8039	Intermediate Similarity	NPD5401	Approved
0.8038	Intermediate Similarity	NPD3817	Phase 2
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD7390	Discontinued
0.7952	Intermediate Similarity	NPD5953	Discontinued
0.795	Intermediate Similarity	NPD5494	Approved
0.7949	Intermediate Similarity	NPD3226	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD920	Approved
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6559	Discontinued
0.7902	Intermediate Similarity	NPD1203	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7892	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7843	Intermediate Similarity	NPD2309	Approved
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7831	Intermediate Similarity	NPD7286	Phase 2
0.7829	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2533	Approved
0.7806	Intermediate Similarity	NPD2532	Approved
0.7806	Intermediate Similarity	NPD2534	Approved
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3268	Approved
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD6100	Approved
0.7748	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7724	Intermediate Similarity	NPD2798	Approved
0.7718	Intermediate Similarity	NPD5124	Phase 1
0.7718	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD9717	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.7662	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD2797	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5405	Approved
0.7632	Intermediate Similarity	NPD5406	Approved
0.7632	Intermediate Similarity	NPD5404	Approved
0.7632	Intermediate Similarity	NPD5408	Approved
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7586	Intermediate Similarity	NPD3225	Approved
0.7586	Intermediate Similarity	NPD4287	Approved
0.7562	Intermediate Similarity	NPD6585	Discontinued
0.7561	Intermediate Similarity	NPD919	Approved
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.7517	Intermediate Similarity	NPD3764	Approved
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7485	Intermediate Similarity	NPD4288	Approved
0.747	Intermediate Similarity	NPD1247	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7436	Intermediate Similarity	NPD7003	Approved
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7415	Intermediate Similarity	NPD3267	Approved
0.7415	Intermediate Similarity	NPD3266	Approved
0.7407	Intermediate Similarity	NPD5889	Approved
0.7407	Intermediate Similarity	NPD5890	Approved
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7374	Intermediate Similarity	NPD4361	Phase 2
0.7374	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7584	Approved
0.7329	Intermediate Similarity	NPD3972	Approved
0.7312	Intermediate Similarity	NPD5049	Phase 3
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD2296	Approved
0.726	Intermediate Similarity	NPD1201	Approved
0.7256	Intermediate Similarity	NPD7577	Discontinued
0.7255	Intermediate Similarity	NPD1933	Approved
0.7251	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5710	Approved
0.7213	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1608	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7213	Phase 3
0.7188	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7212	Phase 2
0.7181	Intermediate Similarity	NPD1164	Approved
0.7172	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD2354	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD447	Suspended
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.712	Intermediate Similarity	NPD6780	Approved
0.712	Intermediate Similarity	NPD6778	Approved
0.712	Intermediate Similarity	NPD6782	Approved
0.712	Intermediate Similarity	NPD6777	Approved
0.712	Intermediate Similarity	NPD6779	Approved
0.712	Intermediate Similarity	NPD6781	Approved
0.712	Intermediate Similarity	NPD6776	Approved
0.7113	Intermediate Similarity	NPD1241	Discontinued
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7871	Phase 2
0.7059	Intermediate Similarity	NPD7870	Phase 2
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD230	Phase 1
0.7025	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2353	Approved
0.702	Intermediate Similarity	NPD1019	Discontinued
0.7019	Intermediate Similarity	NPD7440	Discontinued
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD17	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