NPASS Compound

Structure

NPC474906 OpenBabel07101719122D 34 38 0 0 1 0 0 0 0 0999 V2000 6.7009 0.1909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8511 -0.2040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7315 0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3121 1.8219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 1.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0675 0.8932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9125 1.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0934 -0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5559 -0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1426 0.6957 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9125 0.9457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7818 0.7101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0934 0.4729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0934 2.3644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2744 -0.9457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9034 0.0400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3679 0.1033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1821 1.0328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2744 1.8915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5091 1.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7069 -0.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 0.4729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2744 0.9457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4554 -0.4729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5559 0.7651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0934 3.3101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2245 1.9776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 2.3644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8005 2.2977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5921 0.1128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1775 1.3623 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 2.6653 -0.6872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6593 1.0030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 32 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 12 4 1 6 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 23 1 6 0 0 0 14 19 1 0 0 0 0 14 26 2 0 0 0 0 15 24 1 6 0 0 0 15 33 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 21 1 0 0 0 0 17 34 1 1 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 19 23 1 6 0 0 0 19 28 1 0 0 0 0 20 29 2 0 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 5 1 6 0 0 0 24 9 1 1 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.22
Volume:	466.74
LogP:	2.332
LogD:	1.312
LogS:	-4.334
# Rotatable Bonds:	4
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	6.611
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.275
MDCK Permeability:	7.076184556353837e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.651
Plasma Protein Binding (PPB):	65.79096221923828%
Volume Distribution (VD):	0.56
Pgp-substrate:	44.6480598449707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	6.286
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.655
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.156
Carcinogencity:	0.224
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC474906

Natural Product ID:	NPC474906
*Common Name:**	Ailanthinone
IUPAC Name:	n.a.
Synonyms:	NSC-238187
Standard InCHIKey:	GCIFFNDSOLTCAI-ZTCIHUKBSA-N
Standard InCHI:	InChI=1S/C25H34O9/c1-6-10(2)20(29)34-17-16-12(4)18(27)25(31)22-23(5)13(11(3)7-14(26)19(23)28)8-15(33-21(17)30)24(16,22)9-32-25/h7,10,12-13,15-19,22,27-28,31H,6,8-9H2,1-5H3/t10?,12-,13+,15-,16-,17-,18-,19-,22-,23-,24+,25-/m1/s1
SMILES:	CCC(C)C(=O)O[C@@H]1[C@H]2[C@@H](C)[C@H]([C@@]3([C@@H]4[C@]5(C)[C@@H](C[C@H]([C@@]24CO3)OC1=O)C(=CC(=O)[C@H]5O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487194
PubChem CID:	44559321
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO32507	odyendyea gabonensis	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20738103]
NPO6324	Soulamea tomentosa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264678]

☑ 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
ED50	4
GI50	2
IC50	3
Others	3

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	148.0	%	PMID[518778]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3.4	nM	PMID[518779]
NPT90	Cell Line	DU-145	Homo sapiens	ED50	=	0.09	uM	PMID[518781]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.13	uM	PMID[518781]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.18	uM	PMID[518781]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	31000.0	nM	PMID[518779]
NPT2	Others	Unspecified		INH	=	0.42	uM	PMID[518779]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	32.0	nM	PMID[518779]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	31000.0	nM	PMID[518780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	25.0	%	PMID[518779]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.37	uM	PMID[518781]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.063	ug.mL-1	PMID[518782]

☑ 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 NPC474906 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	241
0.1-0.2	1378
0.2-0.3	4366
0.3-0.4	7948
0.4-0.5	12027
0.5-0.6	7100
0.6-0.7	5259
0.7-0.8	3666
0.8-0.85	587
0.85-0.9	65
0.9-0.95	40
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18547
0.9906	High Similarity	NPC134869
0.9906	High Similarity	NPC235539
0.9906	High Similarity	NPC152199
0.981	High Similarity	NPC289312
0.981	High Similarity	NPC11252
0.9722	High Similarity	NPC297179
0.9714	High Similarity	NPC201992
0.9545	High Similarity	NPC109607
0.9545	High Similarity	NPC107338
0.9537	High Similarity	NPC328374
0.9537	High Similarity	NPC251236
0.9537	High Similarity	NPC96312
0.9537	High Similarity	NPC40632
0.9533	High Similarity	NPC51978
0.9455	High Similarity	NPC476529
0.9455	High Similarity	NPC475775
0.9444	High Similarity	NPC473798
0.9444	High Similarity	NPC469877
0.9444	High Similarity	NPC470919
0.9429	High Similarity	NPC293850
0.9364	High Similarity	NPC188667
0.9364	High Similarity	NPC204552
0.9358	High Similarity	NPC470628
0.9358	High Similarity	NPC474046
0.9358	High Similarity	NPC259306
0.9352	High Similarity	NPC49451
0.9273	High Similarity	NPC309433
0.9259	High Similarity	NPC302146
0.9211	High Similarity	NPC470922
0.9196	High Similarity	NPC112038
0.9189	High Similarity	NPC17772
0.9151	High Similarity	NPC3316
0.9151	High Similarity	NPC144854
0.9115	High Similarity	NPC477046
0.9115	High Similarity	NPC102822
0.9107	High Similarity	NPC469488
0.9099	High Similarity	NPC473968
0.9099	High Similarity	NPC470854
0.9099	High Similarity	NPC97908
0.9099	High Similarity	NPC122033
0.9099	High Similarity	NPC287343
0.9099	High Similarity	NPC474654
0.9083	High Similarity	NPC474516
0.9065	High Similarity	NPC277017
0.9065	High Similarity	NPC154608
0.9065	High Similarity	NPC192813
0.9009	High Similarity	NPC474734
0.9	High Similarity	NPC7921
0.9	High Similarity	NPC208998
0.8981	High Similarity	NPC143706
0.8981	High Similarity	NPC472534
0.8938	High Similarity	NPC470777
0.8929	High Similarity	NPC473590
0.8879	High Similarity	NPC102352
0.8839	High Similarity	NPC16081
0.8839	High Similarity	NPC173686
0.8818	High Similarity	NPC146945
0.8818	High Similarity	NPC171888
0.8807	High Similarity	NPC27814
0.8803	High Similarity	NPC285091
0.8793	High Similarity	NPC265557
0.8793	High Similarity	NPC18945
0.8793	High Similarity	NPC67251
0.8793	High Similarity	NPC105926
0.8793	High Similarity	NPC227397
0.8793	High Similarity	NPC91693
0.8772	High Similarity	NPC127530
0.8772	High Similarity	NPC473920
0.875	High Similarity	NPC243354
0.875	High Similarity	NPC143268
0.875	High Similarity	NPC323821
0.875	High Similarity	NPC268238
0.875	High Similarity	NPC102088
0.875	High Similarity	NPC45218
0.8727	High Similarity	NPC210005
0.8718	High Similarity	NPC476729
0.8718	High Similarity	NPC24651
0.8707	High Similarity	NPC312833
0.8707	High Similarity	NPC471965
0.8704	High Similarity	NPC181357
0.8684	High Similarity	NPC251310
0.8684	High Similarity	NPC470776
0.8673	High Similarity	NPC207217
0.8661	High Similarity	NPC194100
0.8661	High Similarity	NPC62696
0.8661	High Similarity	NPC293038
0.8661	High Similarity	NPC255017
0.8661	High Similarity	NPC194273
0.8655	High Similarity	NPC188291
0.8649	High Similarity	NPC471243
0.8636	High Similarity	NPC141350
0.8632	High Similarity	NPC471961
0.8632	High Similarity	NPC202666
0.8632	High Similarity	NPC478066
0.8632	High Similarity	NPC471964
0.8632	High Similarity	NPC14617
0.8632	High Similarity	NPC262199
0.8624	High Similarity	NPC293512
0.8621	High Similarity	NPC275675
0.8621	High Similarity	NPC470779
0.8609	High Similarity	NPC473401
0.8609	High Similarity	NPC122971
0.8609	High Similarity	NPC319570
0.8596	High Similarity	NPC176513
0.8596	High Similarity	NPC470775
0.8595	High Similarity	NPC100390
0.8595	High Similarity	NPC254614
0.8585	High Similarity	NPC472972
0.8584	High Similarity	NPC475633
0.8571	High Similarity	NPC471967
0.8571	High Similarity	NPC90769
0.8559	High Similarity	NPC30188
0.8559	High Similarity	NPC471962
0.8559	High Similarity	NPC247315
0.8559	High Similarity	NPC177820
0.8559	High Similarity	NPC470477
0.8559	High Similarity	NPC474567
0.8559	High Similarity	NPC471963
0.8547	High Similarity	NPC249848
0.8547	High Similarity	NPC40775
0.8547	High Similarity	NPC235438
0.8547	High Similarity	NPC107966
0.8545	High Similarity	NPC272576
0.8534	High Similarity	NPC471406
0.8522	High Similarity	NPC286347
0.8519	High Similarity	NPC275583
0.8512	High Similarity	NPC262796
0.8512	High Similarity	NPC329993
0.8512	High Similarity	NPC134914
0.8512	High Similarity	NPC172374
0.8512	High Similarity	NPC475377
0.8512	High Similarity	NPC173435
0.8512	High Similarity	NPC45346
0.8512	High Similarity	NPC475167
0.8512	High Similarity	NPC478065
0.8512	High Similarity	NPC264566
0.8512	High Similarity	NPC476074
0.8512	High Similarity	NPC301639
0.8512	High Similarity	NPC478064
0.85	High Similarity	NPC295220
0.85	High Similarity	NPC475636
0.8496	Intermediate Similarity	NPC320118
0.8487	Intermediate Similarity	NPC47113
0.8487	Intermediate Similarity	NPC174367
0.8487	Intermediate Similarity	NPC87662
0.8482	Intermediate Similarity	NPC263827
0.8482	Intermediate Similarity	NPC285410
0.8482	Intermediate Similarity	NPC250481
0.8475	Intermediate Similarity	NPC235405
0.8475	Intermediate Similarity	NPC30735
0.8475	Intermediate Similarity	NPC281148
0.8468	Intermediate Similarity	NPC310546
0.8462	Intermediate Similarity	NPC75417
0.8462	Intermediate Similarity	NPC202051
0.8455	Intermediate Similarity	NPC230541
0.8448	Intermediate Similarity	NPC309780
0.8448	Intermediate Similarity	NPC469945
0.8448	Intermediate Similarity	NPC11551
0.8448	Intermediate Similarity	NPC39211
0.8448	Intermediate Similarity	NPC114441
0.8448	Intermediate Similarity	NPC157868
0.8448	Intermediate Similarity	NPC473884
0.8448	Intermediate Similarity	NPC475171
0.8448	Intermediate Similarity	NPC208381
0.8448	Intermediate Similarity	NPC180550
0.8448	Intermediate Similarity	NPC214484
0.8448	Intermediate Similarity	NPC192791
0.8448	Intermediate Similarity	NPC472949
0.8448	Intermediate Similarity	NPC6377
0.8448	Intermediate Similarity	NPC279143
0.8448	Intermediate Similarity	NPC35405
0.8443	Intermediate Similarity	NPC478153
0.8443	Intermediate Similarity	NPC478152
0.8443	Intermediate Similarity	NPC471855
0.8443	Intermediate Similarity	NPC478150
0.8443	Intermediate Similarity	NPC102316
0.844	Intermediate Similarity	NPC475036
0.844	Intermediate Similarity	NPC65523
0.8435	Intermediate Similarity	NPC477252
0.8435	Intermediate Similarity	NPC224121
0.843	Intermediate Similarity	NPC54614
0.843	Intermediate Similarity	NPC309096
0.8421	Intermediate Similarity	NPC472274
0.8417	Intermediate Similarity	NPC470780
0.8407	Intermediate Similarity	NPC477253
0.8407	Intermediate Similarity	NPC280782
0.8407	Intermediate Similarity	NPC116794
0.8407	Intermediate Similarity	NPC472002
0.8407	Intermediate Similarity	NPC474927
0.8407	Intermediate Similarity	NPC130427
0.8403	Intermediate Similarity	NPC473255
0.84	Intermediate Similarity	NPC596
0.8393	Intermediate Similarity	NPC102914
0.8393	Intermediate Similarity	NPC274507
0.8393	Intermediate Similarity	NPC474786
0.8393	Intermediate Similarity	NPC220984
0.8393	Intermediate Similarity	NPC199457
0.8393	Intermediate Similarity	NPC137104
0.8393	Intermediate Similarity	NPC75747

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 NPC474906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1628
0.2-0.3	3834
0.3-0.4	2207
0.4-0.5	711
0.5-0.6	288
0.6-0.7	125
0.7-0.8	129
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD8328	Phase 3
0.8276	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7492	Approved
0.8246	Intermediate Similarity	NPD8297	Approved
0.8246	Intermediate Similarity	NPD6882	Approved
0.822	Intermediate Similarity	NPD6319	Approved
0.822	Intermediate Similarity	NPD6059	Approved
0.822	Intermediate Similarity	NPD6054	Approved
0.8198	Intermediate Similarity	NPD6402	Approved
0.8198	Intermediate Similarity	NPD5739	Approved
0.8198	Intermediate Similarity	NPD7128	Approved
0.8198	Intermediate Similarity	NPD6675	Approved
0.8197	Intermediate Similarity	NPD7736	Approved
0.8182	Intermediate Similarity	NPD6616	Approved
0.8142	Intermediate Similarity	NPD6372	Approved
0.8142	Intermediate Similarity	NPD6373	Approved
0.8142	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6412	Phase 2
0.812	Intermediate Similarity	NPD6009	Approved
0.8115	Intermediate Similarity	NPD8293	Discontinued
0.8115	Intermediate Similarity	NPD7078	Approved
0.8083	Intermediate Similarity	NPD6370	Approved
0.8053	Intermediate Similarity	NPD6881	Approved
0.8053	Intermediate Similarity	NPD7320	Approved
0.8053	Intermediate Similarity	NPD6899	Approved
0.8017	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD6016	Approved
0.8	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6015	Approved
0.8	Intermediate Similarity	NPD6650	Approved
0.7965	Intermediate Similarity	NPD5701	Approved
0.7965	Intermediate Similarity	NPD5697	Approved
0.7934	Intermediate Similarity	NPD5988	Approved
0.7913	Intermediate Similarity	NPD7102	Approved
0.7913	Intermediate Similarity	NPD6883	Approved
0.7913	Intermediate Similarity	NPD7290	Approved
0.7895	Intermediate Similarity	NPD6686	Approved
0.7886	Intermediate Similarity	NPD7507	Approved
0.7845	Intermediate Similarity	NPD6617	Approved
0.7845	Intermediate Similarity	NPD6847	Approved
0.7845	Intermediate Similarity	NPD6869	Approved
0.7845	Intermediate Similarity	NPD8130	Phase 1
0.7826	Intermediate Similarity	NPD6014	Approved
0.7826	Intermediate Similarity	NPD6012	Approved
0.7826	Intermediate Similarity	NPD6013	Approved
0.7739	Intermediate Similarity	NPD6011	Approved
0.7739	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7604	Phase 2
0.7705	Intermediate Similarity	NPD5983	Phase 2
0.7698	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6033	Approved
0.7615	Intermediate Similarity	NPD7748	Approved
0.76	Intermediate Similarity	NPD6336	Discontinued
0.7593	Intermediate Similarity	NPD7515	Phase 2
0.7568	Intermediate Similarity	NPD6084	Phase 2
0.7568	Intermediate Similarity	NPD6083	Phase 2
0.7568	Intermediate Similarity	NPD7902	Approved
0.7568	Intermediate Similarity	NPD4755	Approved
0.7565	Intermediate Similarity	NPD6008	Approved
0.7521	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4634	Approved
0.7438	Intermediate Similarity	NPD6274	Approved
0.7434	Intermediate Similarity	NPD5285	Approved
0.7434	Intermediate Similarity	NPD5286	Approved
0.7434	Intermediate Similarity	NPD4700	Approved
0.7434	Intermediate Similarity	NPD4696	Approved
0.7407	Intermediate Similarity	NPD5328	Approved
0.7398	Intermediate Similarity	NPD7101	Approved
0.7398	Intermediate Similarity	NPD7516	Approved
0.7398	Intermediate Similarity	NPD7100	Approved
0.7377	Intermediate Similarity	NPD7115	Discovery
0.7364	Intermediate Similarity	NPD6399	Phase 3
0.7345	Intermediate Similarity	NPD7638	Approved
0.7321	Intermediate Similarity	NPD5222	Approved
0.7321	Intermediate Similarity	NPD5221	Approved
0.7321	Intermediate Similarity	NPD4697	Phase 3
0.7321	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6335	Approved
0.7317	Intermediate Similarity	NPD7327	Approved
0.7317	Intermediate Similarity	NPD7328	Approved
0.7315	Intermediate Similarity	NPD6672	Approved
0.7315	Intermediate Similarity	NPD5737	Approved
0.7311	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5225	Approved
0.7304	Intermediate Similarity	NPD4633	Approved
0.7304	Intermediate Similarity	NPD5226	Approved
0.7304	Intermediate Similarity	NPD5224	Approved
0.7304	Intermediate Similarity	NPD5211	Phase 2
0.7297	Intermediate Similarity	NPD7900	Approved
0.7297	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6868	Approved
0.7281	Intermediate Similarity	NPD7639	Approved
0.7281	Intermediate Similarity	NPD7640	Approved
0.728	Intermediate Similarity	NPD8033	Approved
0.728	Intermediate Similarity	NPD8517	Approved
0.728	Intermediate Similarity	NPD6908	Approved
0.728	Intermediate Similarity	NPD8515	Approved
0.728	Intermediate Similarity	NPD8516	Approved
0.728	Intermediate Similarity	NPD6909	Approved
0.728	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD6079	Approved
0.7265	Intermediate Similarity	NPD4768	Approved
0.7265	Intermediate Similarity	NPD4767	Approved
0.7257	Intermediate Similarity	NPD5173	Approved
0.7241	Intermediate Similarity	NPD5175	Approved
0.7241	Intermediate Similarity	NPD5174	Approved
0.7236	Intermediate Similarity	NPD6317	Approved
0.7232	Intermediate Similarity	NPD5695	Phase 3
0.7222	Intermediate Similarity	NPD3573	Approved
0.7217	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD8294	Approved
0.72	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD4225	Approved
0.7193	Intermediate Similarity	NPD5696	Approved
0.7179	Intermediate Similarity	NPD5141	Approved
0.7177	Intermediate Similarity	NPD6314	Approved
0.7177	Intermediate Similarity	NPD6313	Approved
0.7165	Intermediate Similarity	NPD6067	Discontinued
0.7143	Intermediate Similarity	NPD8380	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD6921	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.713	Intermediate Similarity	NPD3618	Phase 1
0.7117	Intermediate Similarity	NPD6411	Approved
0.7107	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4754	Approved
0.7059	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD46	Approved
0.7027	Intermediate Similarity	NPD6698	Approved
0.7025	Intermediate Similarity	NPD5251	Approved
0.7025	Intermediate Similarity	NPD5250	Approved
0.7025	Intermediate Similarity	NPD5249	Phase 3
0.7025	Intermediate Similarity	NPD5248	Approved
0.7025	Intermediate Similarity	NPD5247	Approved
0.7008	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7334	Approved
0.6972	Remote Similarity	NPD6409	Approved
0.6972	Remote Similarity	NPD7146	Approved
0.6972	Remote Similarity	NPD5330	Approved
0.6972	Remote Similarity	NPD6684	Approved
0.6972	Remote Similarity	NPD7521	Approved
0.6944	Remote Similarity	NPD4786	Approved
0.6937	Remote Similarity	NPD6673	Approved
0.6937	Remote Similarity	NPD6904	Approved
0.6937	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6080	Approved
0.6937	Remote Similarity	NPD6101	Approved
0.6937	Remote Similarity	NPD4753	Phase 2
0.6917	Remote Similarity	NPD7260	Phase 2
0.6916	Remote Similarity	NPD3667	Approved
0.6903	Remote Similarity	NPD4202	Approved
0.6891	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8074	Phase 3
0.6847	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD5956	Approved
0.6842	Remote Similarity	NPD5282	Discontinued
0.6829	Remote Similarity	NPD5215	Approved
0.6829	Remote Similarity	NPD5216	Approved
0.6829	Remote Similarity	NPD5217	Approved
0.6814	Remote Similarity	NPD8034	Phase 2
0.6814	Remote Similarity	NPD8035	Phase 2
0.6789	Remote Similarity	NPD3666	Approved
0.6789	Remote Similarity	NPD3133	Approved
0.6789	Remote Similarity	NPD3665	Phase 1
0.6783	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6053	Discontinued
0.6754	Remote Similarity	NPD5779	Approved
0.6754	Remote Similarity	NPD5778	Approved
0.6748	Remote Similarity	NPD5169	Approved
0.6748	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5135	Approved
0.6741	Remote Similarity	NPD6845	Suspended
0.6729	Remote Similarity	NPD4695	Discontinued
0.6727	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7632	Discontinued
0.6721	Remote Similarity	NPD5168	Approved
0.6694	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6050	Approved
0.6639	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5344	Discontinued
0.6638	Remote Similarity	NPD4629	Approved
0.6638	Remote Similarity	NPD5210	Approved
0.6619	Remote Similarity	NPD6333	Approved
0.6619	Remote Similarity	NPD6334	Approved
0.6579	Remote Similarity	NPD5692	Phase 3
0.6577	Remote Similarity	NPD5329	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