NPASS Compound

Structure

NPC187545 OpenBabel07101719252D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.3729 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2162 2.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0594 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 30 1 6 0 0 0 20 31 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 25 1 1 0 0 0 23 29 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.34
Volume:	497.246
LogP:	3.942
LogD:	3.794
LogS:	-4.084
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	5.308
Fsp3:	0.897
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	7.465916041837772e-06
Pgp-inhibitor:	0.415
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.497
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.479
Plasma Protein Binding (PPB):	75.9049072265625%
Volume Distribution (VD):	0.43
Pgp-substrate:	16.50933074951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.53
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.355
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	3.552
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.675
Carcinogencity:	0.662
Eye Corrosion:	0.012
Eye Irritation:	0.02
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC187545

Natural Product ID:	NPC187545
*Common Name:**	3Beta,21Beta-Dihydroxy-30-(D:A)-Friedo-Olean-20(29)-En-27-Oic Acid
IUPAC Name:	(3S,4R,4aS,6aS,6aR,6bR,8aS,10S,12aR,14aS,14bS)-3,10-dihydroxy-4,4a,6b,8a,14a-pentamethyl-11-methylidene-1,2,3,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-hexadecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	IYUZPBQOICRGRP-BCXJXKNISA-N
Standard InCHI:	InChI=1S/C29H46O4/c1-17-15-23-25(3,16-20(17)31)11-13-28(6)22-9-10-26(4)18(2)19(30)7-8-21(26)27(22,5)12-14-29(23,28)24(32)33/h18-23,30-31H,1,7-16H2,2-6H3,(H,32,33)/t18-,19-,20-,21+,22-,23+,25-,26+,27-,28+,29-/m0/s1
SMILES:	C=C1C[C@@H]2[C@@](C)(CC[C@]3(C)[C@H]4CC[C@]5(C)[C@@H](C)[C@H](CC[C@H]5[C@]4(C)CC[C@@]23C(=O)O)O)C[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035573
PubChem CID:	70683828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22360639]
NPO13364	Caloncoba glauca	Species	Achariaceae	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
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	<	50.0	%	PMID[506330]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	<	50.0	%	PMID[506330]
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	Inhibition	<	50.0	%	PMID[506330]
NPT4861	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Mus musculus	Inhibition	<	50.0	%	PMID[506330]

☑ 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 NPC187545 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	228
0.1-0.2	1746
0.2-0.3	6139
0.3-0.4	15847
0.4-0.5	7580
0.5-0.6	5101
0.6-0.7	4189
0.7-0.8	1493
0.8-0.85	220
0.85-0.9	152
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC16377
0.9059	High Similarity	NPC52169
0.9059	High Similarity	NPC182797
0.9048	High Similarity	NPC2783
0.8953	High Similarity	NPC290972
0.8953	High Similarity	NPC234346
0.8953	High Similarity	NPC143232
0.8953	High Similarity	NPC263393
0.8953	High Similarity	NPC127689
0.8953	High Similarity	NPC61543
0.8953	High Similarity	NPC64872
0.8953	High Similarity	NPC270768
0.8953	High Similarity	NPC121798
0.8953	High Similarity	NPC59263
0.8953	High Similarity	NPC198664
0.8953	High Similarity	NPC293048
0.8953	High Similarity	NPC25906
0.8953	High Similarity	NPC225585
0.8953	High Similarity	NPC130520
0.8953	High Similarity	NPC274330
0.8941	High Similarity	NPC33768
0.8941	High Similarity	NPC307426
0.8941	High Similarity	NPC130577
0.8941	High Similarity	NPC264005
0.8941	High Similarity	NPC293564
0.8941	High Similarity	NPC102683
0.8941	High Similarity	NPC171203
0.8941	High Similarity	NPC269360
0.8941	High Similarity	NPC142415
0.8941	High Similarity	NPC68160
0.8941	High Similarity	NPC242468
0.8941	High Similarity	NPC18064
0.8941	High Similarity	NPC88716
0.8941	High Similarity	NPC98442
0.8941	High Similarity	NPC51700
0.8929	High Similarity	NPC264317
0.8929	High Similarity	NPC294438
0.8889	High Similarity	NPC470425
0.8851	High Similarity	NPC227467
0.8851	High Similarity	NPC291028
0.8851	High Similarity	NPC290614
0.8851	High Similarity	NPC18872
0.8851	High Similarity	NPC130278
0.8851	High Similarity	NPC210037
0.8851	High Similarity	NPC470589
0.8851	High Similarity	NPC120968
0.8851	High Similarity	NPC111110
0.8851	High Similarity	NPC273621
0.8851	High Similarity	NPC126369
0.8851	High Similarity	NPC477872
0.8851	High Similarity	NPC7260
0.8837	High Similarity	NPC181225
0.8837	High Similarity	NPC290690
0.8837	High Similarity	NPC474719
0.8837	High Similarity	NPC473242
0.8837	High Similarity	NPC246708
0.8837	High Similarity	NPC17733
0.8837	High Similarity	NPC470629
0.8837	High Similarity	NPC474512
0.8837	High Similarity	NPC40552
0.8824	High Similarity	NPC12774
0.8824	High Similarity	NPC72638
0.8778	High Similarity	NPC116457
0.8764	High Similarity	NPC91010
0.8764	High Similarity	NPC87095
0.875	High Similarity	NPC324341
0.875	High Similarity	NPC105189
0.875	High Similarity	NPC282616
0.875	High Similarity	NPC233455
0.875	High Similarity	NPC235884
0.875	High Similarity	NPC472149
0.875	High Similarity	NPC65120
0.875	High Similarity	NPC84319
0.875	High Similarity	NPC52021
0.875	High Similarity	NPC966
0.875	High Similarity	NPC71074
0.875	High Similarity	NPC145067
0.875	High Similarity	NPC228784
0.875	High Similarity	NPC25299
0.875	High Similarity	NPC288833
0.875	High Similarity	NPC187722
0.875	High Similarity	NPC158030
0.875	High Similarity	NPC300351
0.875	High Similarity	NPC306541
0.875	High Similarity	NPC4036
0.875	High Similarity	NPC474525
0.875	High Similarity	NPC155120
0.8736	High Similarity	NPC220498
0.8736	High Similarity	NPC57954
0.8736	High Similarity	NPC474972
0.8736	High Similarity	NPC95246
0.8736	High Similarity	NPC213832
0.8736	High Similarity	NPC281524
0.8736	High Similarity	NPC161751
0.8736	High Similarity	NPC474686
0.8736	High Similarity	NPC470588
0.8706	High Similarity	NPC292553
0.8681	High Similarity	NPC189880
0.8667	High Similarity	NPC290481
0.8652	High Similarity	NPC307335
0.8652	High Similarity	NPC295643
0.8652	High Similarity	NPC118519
0.8652	High Similarity	NPC158059
0.8652	High Similarity	NPC202728
0.8652	High Similarity	NPC74855
0.8652	High Similarity	NPC298554
0.8652	High Similarity	NPC275809
0.8652	High Similarity	NPC136313
0.8652	High Similarity	NPC214756
0.8652	High Similarity	NPC272075
0.8652	High Similarity	NPC229281
0.8652	High Similarity	NPC86368
0.8642	High Similarity	NPC474433
0.8636	High Similarity	NPC193750
0.8636	High Similarity	NPC474728
0.8636	High Similarity	NPC86372
0.8636	High Similarity	NPC172361
0.8636	High Similarity	NPC113989
0.8636	High Similarity	NPC169933
0.8636	High Similarity	NPC46441
0.8636	High Similarity	NPC49320
0.8636	High Similarity	NPC120840
0.8625	High Similarity	NPC144075
0.8621	High Similarity	NPC471900
0.8621	High Similarity	NPC4309
0.8605	High Similarity	NPC472738
0.8588	High Similarity	NPC171789
0.8587	High Similarity	NPC174663
0.8556	High Similarity	NPC191412
0.8556	High Similarity	NPC282395
0.8556	High Similarity	NPC263548
0.8556	High Similarity	NPC231063
0.8556	High Similarity	NPC145667
0.8556	High Similarity	NPC114159
0.8556	High Similarity	NPC299996
0.8556	High Similarity	NPC222047
0.8556	High Similarity	NPC20235
0.8556	High Similarity	NPC209868
0.8556	High Similarity	NPC88116
0.8556	High Similarity	NPC6818
0.8556	High Similarity	NPC159365
0.8556	High Similarity	NPC469982
0.8556	High Similarity	NPC32407
0.8556	High Similarity	NPC474529
0.8539	High Similarity	NPC60755
0.8539	High Similarity	NPC285184
0.8539	High Similarity	NPC475708
0.8539	High Similarity	NPC6255
0.8539	High Similarity	NPC38754
0.8539	High Similarity	NPC471588
0.8539	High Similarity	NPC198054
0.8539	High Similarity	NPC470590
0.8539	High Similarity	NPC77099
0.8537	High Similarity	NPC472608
0.8523	High Similarity	NPC271974
0.8523	High Similarity	NPC247312
0.8523	High Similarity	NPC30522
0.8506	High Similarity	NPC4643
0.8506	High Similarity	NPC71507
0.8488	Intermediate Similarity	NPC133954
0.8471	Intermediate Similarity	NPC475726
0.8471	Intermediate Similarity	NPC243347
0.8471	Intermediate Similarity	NPC471037
0.8471	Intermediate Similarity	NPC472743
0.8462	Intermediate Similarity	NPC473240
0.8462	Intermediate Similarity	NPC139570
0.8462	Intermediate Similarity	NPC474727
0.8462	Intermediate Similarity	NPC96916
0.8462	Intermediate Similarity	NPC148523
0.8462	Intermediate Similarity	NPC198245
0.8452	Intermediate Similarity	NPC328264
0.8444	Intermediate Similarity	NPC291373
0.8444	Intermediate Similarity	NPC49776
0.8444	Intermediate Similarity	NPC471902
0.8444	Intermediate Similarity	NPC244356
0.8444	Intermediate Similarity	NPC473690
0.8444	Intermediate Similarity	NPC474436
0.8444	Intermediate Similarity	NPC474806
0.8444	Intermediate Similarity	NPC224060
0.8444	Intermediate Similarity	NPC133579
0.8444	Intermediate Similarity	NPC118490
0.8444	Intermediate Similarity	NPC63118
0.8444	Intermediate Similarity	NPC287118
0.8391	Intermediate Similarity	NPC168231
0.8391	Intermediate Similarity	NPC475862
0.8391	Intermediate Similarity	NPC70661
0.8391	Intermediate Similarity	NPC477579
0.8391	Intermediate Similarity	NPC73038
0.8391	Intermediate Similarity	NPC95594
0.8391	Intermediate Similarity	NPC56588
0.8391	Intermediate Similarity	NPC74363
0.8391	Intermediate Similarity	NPC322159
0.8391	Intermediate Similarity	NPC213412
0.8391	Intermediate Similarity	NPC235341
0.8375	Intermediate Similarity	NPC211009
0.8375	Intermediate Similarity	NPC36310
0.8372	Intermediate Similarity	NPC474482
0.8372	Intermediate Similarity	NPC130966
0.8372	Intermediate Similarity	NPC263974
0.8372	Intermediate Similarity	NPC264665

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 NPC187545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	2209
0.2-0.3	3940
0.3-0.4	1901
0.4-0.5	481
0.5-0.6	239
0.6-0.7	138
0.7-0.8	16
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD7520	Clinical (unspecified phase)
0.875	High Similarity	NPD7515	Phase 2
0.8352	Intermediate Similarity	NPD7748	Approved
0.8333	Intermediate Similarity	NPD8034	Phase 2
0.8333	Intermediate Similarity	NPD8035	Phase 2
0.8085	Intermediate Similarity	NPD7902	Approved
0.7857	Intermediate Similarity	NPD6117	Approved
0.7766	Intermediate Similarity	NPD7900	Approved
0.7766	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6116	Phase 1
0.7674	Intermediate Similarity	NPD6115	Approved
0.7674	Intermediate Similarity	NPD6114	Approved
0.7674	Intermediate Similarity	NPD6697	Approved
0.7674	Intermediate Similarity	NPD6118	Approved
0.7619	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7363	Intermediate Similarity	NPD4786	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD3667	Approved
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7253	Intermediate Similarity	NPD4788	Approved
0.7188	Intermediate Similarity	NPD6079	Approved
0.7176	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7525	Registered
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8133	Approved
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD4202	Approved
0.6932	Remote Similarity	NPD3703	Phase 2
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD5211	Phase 2
0.6887	Remote Similarity	NPD6899	Approved
0.6887	Remote Similarity	NPD7320	Approved
0.6887	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD4244	Approved
0.686	Remote Similarity	NPD4245	Approved
0.6847	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD6411	Approved
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD5173	Approved
0.6832	Remote Similarity	NPD6083	Phase 2
0.6832	Remote Similarity	NPD4755	Approved
0.6822	Remote Similarity	NPD6373	Approved
0.6822	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6372	Approved
0.6809	Remote Similarity	NPD3668	Phase 3
0.6792	Remote Similarity	NPD5701	Approved
0.6792	Remote Similarity	NPD5697	Approved
0.6786	Remote Similarity	NPD4224	Phase 2
0.6782	Remote Similarity	NPD6081	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6762	Remote Similarity	NPD5141	Approved
0.6759	Remote Similarity	NPD6883	Approved
0.6759	Remote Similarity	NPD7290	Approved
0.6759	Remote Similarity	NPD7102	Approved
0.6744	Remote Similarity	NPD3698	Phase 2
0.6733	Remote Similarity	NPD7614	Phase 1
0.6729	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6011	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD6903	Approved
0.6701	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD4700	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6697	Remote Similarity	NPD6847	Approved
0.6697	Remote Similarity	NPD6650	Approved
0.6697	Remote Similarity	NPD6617	Approved
0.6697	Remote Similarity	NPD6869	Approved
0.6697	Remote Similarity	NPD6649	Approved
0.6697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8130	Phase 1
0.6696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6638	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5223	Approved
0.6633	Remote Similarity	NPD4753	Phase 2
0.6633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6101	Approved
0.6628	Remote Similarity	NPD5360	Phase 3
0.6628	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD5778	Approved
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5777	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5224	Approved
0.6559	Remote Similarity	NPD4695	Discontinued
0.6556	Remote Similarity	NPD6942	Approved
0.6556	Remote Similarity	NPD7339	Approved
0.6522	Remote Similarity	NPD3671	Phase 1
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.6495	Remote Similarity	NPD5279	Phase 3
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4623	Approved
0.6495	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5695	Phase 3
0.6471	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6868	Approved
0.6442	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD6686	Approved
0.6421	Remote Similarity	NPD4221	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6408	Remote Similarity	NPD7732	Phase 3
0.6392	Remote Similarity	NPD5329	Approved
0.6389	Remote Similarity	NPD4767	Approved
0.6389	Remote Similarity	NPD4768	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6374	Remote Similarity	NPD3702	Approved
0.6364	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5362	Discontinued
0.6348	Remote Similarity	NPD6335	Approved
0.6344	Remote Similarity	NPD3617	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD7637	Suspended
0.6337	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD6412	Phase 2
0.6327	Remote Similarity	NPD6098	Approved
0.6316	Remote Similarity	NPD6274	Approved
0.6311	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD5210	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6673	Approved
0.63	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD6904	Approved
0.6293	Remote Similarity	NPD7100	Approved
0.6293	Remote Similarity	NPD7101	Approved
0.6289	Remote Similarity	NPD4197	Approved
0.6273	Remote Similarity	NPD5168	Approved
0.6273	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4730	Approved
0.6273	Remote Similarity	NPD5128	Approved
0.6261	Remote Similarity	NPD6317	Approved
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6008	Approved
0.623	Remote Similarity	NPD7319	Approved
0.6226	Remote Similarity	NPD8418	Phase 2
0.6224	Remote Similarity	NPD1694	Approved
0.6222	Remote Similarity	NPD4758	Discontinued
0.6207	Remote Similarity	NPD6314	Approved
0.6207	Remote Similarity	NPD6313	Approved
0.6196	Remote Similarity	NPD8264	Approved
0.6186	Remote Similarity	NPD7154	Phase 3
0.6186	Remote Similarity	NPD6908	Approved
0.6186	Remote Similarity	NPD6909	Approved
0.6176	Remote Similarity	NPD5693	Phase 1
0.617	Remote Similarity	NPD5364	Discontinued
0.6162	Remote Similarity	NPD4138	Approved
0.6162	Remote Similarity	NPD4690	Approved
0.6162	Remote Similarity	NPD4693	Phase 3
0.6162	Remote Similarity	NPD4689	Approved
0.6162	Remote Similarity	NPD5205	Approved
0.6162	Remote Similarity	NPD4688	Approved
0.6161	Remote Similarity	NPD5169	Approved
0.6161	Remote Similarity	NPD5250	Approved
0.6161	Remote Similarity	NPD5249	Phase 3
0.6161	Remote Similarity	NPD5134	Clinical (unspecified phase)

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