NPASS Compound

Structure

CID147066 OpenBabel06191715522D 33 36 0 0 1 0 0 0 0 0999 V2000 0.0789 6.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4621 5.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6692 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0970 4.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2728 3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4934 5.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8138 2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0874 -1.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2102 3.4269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3861 1.7490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 11 12 1 0 0 0 0 11 23 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 20 10 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	509.035
LogP:	7.116
LogD:	5.106
LogS:	-5.252
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	4.68
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.328
MDCK Permeability:	1.0107925845659338e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.333
Plasma Protein Binding (PPB):	95.81431579589844%
Volume Distribution (VD):	0.795
Pgp-substrate:	2.3808765411376953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.407
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	9.511
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.138
Carcinogencity:	0.351
Eye Corrosion:	0.009
Eye Irritation:	0.069
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC147066

Natural Product ID:	NPC147066
*Common Name:**	3-Oxotirucalla-7,24-Dien-21-Oic Acid
IUPAC Name:	(2S)-6-methyl-2-[(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid
Synonyms:
Standard InCHIKey:	PYHNHGARAGBCRY-ZYHXIRFQSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,20-22,24H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,28+,29-,30+/m0/s1
SMILES:	CC(=CCC[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481824
PubChem CID:	158100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	Species	Rosaceae	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
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	=	20.0	ug.mL-1	PMID[458504]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	90.0	%	PMID[458504]

☑ 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 NPC147066 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	146
0.1-0.2	1052
0.2-0.3	5966
0.3-0.4	15910
0.4-0.5	6681
0.5-0.6	6281
0.6-0.7	4271
0.7-0.8	1993
0.8-0.85	279
0.85-0.9	90
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC201912
0.9737	High Similarity	NPC38350
0.9733	High Similarity	NPC477371
0.961	High Similarity	NPC320514
0.961	High Similarity	NPC260956
0.9494	High Similarity	NPC29447
0.9487	High Similarity	NPC69279
0.9487	High Similarity	NPC83569
0.9481	High Similarity	NPC477372
0.9359	High Similarity	NPC133391
0.9259	High Similarity	NPC96496
0.9259	High Similarity	NPC136948
0.9241	High Similarity	NPC477373
0.9221	High Similarity	NPC215843
0.9221	High Similarity	NPC158846
0.9136	High Similarity	NPC155011
0.9036	High Similarity	NPC262043
0.9036	High Similarity	NPC474570
0.9024	High Similarity	NPC142361
0.9024	High Similarity	NPC474684
0.9	High Similarity	NPC167103
0.9	High Similarity	NPC470015
0.9	High Similarity	NPC477852
0.9	High Similarity	NPC168188
0.8987	High Similarity	NPC274050
0.8987	High Similarity	NPC278459
0.8987	High Similarity	NPC263272
0.8987	High Similarity	NPC267691
0.8987	High Similarity	NPC162632
0.8987	High Similarity	NPC471898
0.8974	High Similarity	NPC231431
0.8974	High Similarity	NPC192744
0.8961	High Similarity	NPC471899
0.8961	High Similarity	NPC107039
0.8961	High Similarity	NPC66105
0.8961	High Similarity	NPC165711
0.8961	High Similarity	NPC471897
0.8947	High Similarity	NPC192540
0.8947	High Similarity	NPC279666
0.8889	High Similarity	NPC221758
0.8889	High Similarity	NPC82902
0.8889	High Similarity	NPC85774
0.8889	High Similarity	NPC165064
0.8889	High Similarity	NPC59453
0.8889	High Similarity	NPC214043
0.8875	High Similarity	NPC69101
0.8875	High Similarity	NPC193347
0.8875	High Similarity	NPC251779
0.8861	High Similarity	NPC37038
0.8846	High Similarity	NPC260385
0.8846	High Similarity	NPC280654
0.8846	High Similarity	NPC110094
0.8831	High Similarity	NPC69143
0.8831	High Similarity	NPC89294
0.8831	High Similarity	NPC246445
0.8831	High Similarity	NPC20466
0.8824	High Similarity	NPC154101
0.8816	High Similarity	NPC283908
0.8816	High Similarity	NPC183503
0.8816	High Similarity	NPC161923
0.8816	High Similarity	NPC476046
0.8816	High Similarity	NPC241854
0.8816	High Similarity	NPC103958
0.8816	High Similarity	NPC251970
0.881	High Similarity	NPC475921
0.881	High Similarity	NPC474704
0.88	High Similarity	NPC160817
0.8795	High Similarity	NPC187376
0.8795	High Similarity	NPC159046
0.8795	High Similarity	NPC233836
0.878	High Similarity	NPC123319
0.878	High Similarity	NPC471224
0.878	High Similarity	NPC474218
0.878	High Similarity	NPC269638
0.878	High Similarity	NPC469948
0.878	High Similarity	NPC94531
0.878	High Similarity	NPC311702
0.878	High Similarity	NPC470223
0.8765	High Similarity	NPC70834
0.875	High Similarity	NPC142244
0.8734	High Similarity	NPC16394
0.8734	High Similarity	NPC196827
0.8734	High Similarity	NPC199595
0.8734	High Similarity	NPC274996
0.8718	High Similarity	NPC68828
0.8718	High Similarity	NPC212661
0.8718	High Similarity	NPC471035
0.8706	High Similarity	NPC471896
0.8684	High Similarity	NPC161187
0.8684	High Similarity	NPC244708
0.8684	High Similarity	NPC330659
0.8675	High Similarity	NPC28252
0.8675	High Similarity	NPC474732
0.8675	High Similarity	NPC51014
0.8675	High Similarity	NPC55309
0.8675	High Similarity	NPC469994
0.8675	High Similarity	NPC474733
0.8675	High Similarity	NPC31564
0.8675	High Similarity	NPC145879
0.8675	High Similarity	NPC474778
0.8659	High Similarity	NPC144258
0.8659	High Similarity	NPC473246
0.8659	High Similarity	NPC96095
0.8659	High Similarity	NPC194937
0.8659	High Similarity	NPC476038
0.8659	High Similarity	NPC164577
0.8659	High Similarity	NPC237712
0.8642	High Similarity	NPC100297
0.8642	High Similarity	NPC472239
0.8642	High Similarity	NPC240302
0.8642	High Similarity	NPC151519
0.8625	High Similarity	NPC472478
0.8625	High Similarity	NPC104545
0.8608	High Similarity	NPC82635
0.8608	High Similarity	NPC321514
0.8608	High Similarity	NPC179028
0.8608	High Similarity	NPC321690
0.8605	High Similarity	NPC204341
0.8605	High Similarity	NPC86266
0.8605	High Similarity	NPC189520
0.8605	High Similarity	NPC212301
0.8605	High Similarity	NPC110657
0.859	High Similarity	NPC309399
0.859	High Similarity	NPC180886
0.8588	High Similarity	NPC215029
0.8588	High Similarity	NPC102414
0.8588	High Similarity	NPC54689
0.8588	High Similarity	NPC476733
0.8588	High Similarity	NPC84271
0.8588	High Similarity	NPC77168
0.8571	High Similarity	NPC58063
0.8571	High Similarity	NPC128644
0.8571	High Similarity	NPC90652
0.8571	High Similarity	NPC317590
0.8571	High Similarity	NPC167877
0.8571	High Similarity	NPC93778
0.8571	High Similarity	NPC475740
0.8554	High Similarity	NPC474083
0.8554	High Similarity	NPC283733
0.8554	High Similarity	NPC11711
0.8554	High Similarity	NPC473038
0.8554	High Similarity	NPC474537
0.8537	High Similarity	NPC310470
0.8537	High Similarity	NPC97913
0.8537	High Similarity	NPC472740
0.8523	High Similarity	NPC469599
0.8519	High Similarity	NPC221647
0.8506	High Similarity	NPC170220
0.8506	High Similarity	NPC152897
0.8506	High Similarity	NPC107674
0.8506	High Similarity	NPC141497
0.8506	High Similarity	NPC470224
0.8506	High Similarity	NPC470376
0.8506	High Similarity	NPC66429
0.8506	High Similarity	NPC470375
0.8488	Intermediate Similarity	NPC175628
0.8488	Intermediate Similarity	NPC111585
0.8488	Intermediate Similarity	NPC148414
0.8481	Intermediate Similarity	NPC472300
0.8471	Intermediate Similarity	NPC328313
0.8471	Intermediate Similarity	NPC28227
0.8471	Intermediate Similarity	NPC242864
0.8471	Intermediate Similarity	NPC470417
0.8471	Intermediate Similarity	NPC117122
0.8462	Intermediate Similarity	NPC476844
0.8462	Intermediate Similarity	NPC201027
0.8452	Intermediate Similarity	NPC473168
0.8452	Intermediate Similarity	NPC195640
0.8452	Intermediate Similarity	NPC472869
0.8452	Intermediate Similarity	NPC186975
0.8452	Intermediate Similarity	NPC264127
0.8434	Intermediate Similarity	NPC58841
0.8434	Intermediate Similarity	NPC156981
0.8434	Intermediate Similarity	NPC329043
0.8434	Intermediate Similarity	NPC472865
0.8434	Intermediate Similarity	NPC19849
0.8434	Intermediate Similarity	NPC472864
0.8434	Intermediate Similarity	NPC472480
0.8434	Intermediate Similarity	NPC321187
0.8434	Intermediate Similarity	NPC161423
0.8434	Intermediate Similarity	NPC227064
0.8434	Intermediate Similarity	NPC209882
0.8415	Intermediate Similarity	NPC327969
0.8415	Intermediate Similarity	NPC296367
0.8415	Intermediate Similarity	NPC3511
0.8415	Intermediate Similarity	NPC472867
0.8415	Intermediate Similarity	NPC321289
0.8415	Intermediate Similarity	NPC238991
0.8415	Intermediate Similarity	NPC142253
0.8415	Intermediate Similarity	NPC302661
0.8409	Intermediate Similarity	NPC49670
0.8409	Intermediate Similarity	NPC159410
0.84	Intermediate Similarity	NPC20610
0.8395	Intermediate Similarity	NPC2482
0.8395	Intermediate Similarity	NPC267517
0.8395	Intermediate Similarity	NPC477057
0.8391	Intermediate Similarity	NPC26888
0.8391	Intermediate Similarity	NPC297265
0.8375	Intermediate Similarity	NPC63020
0.8375	Intermediate Similarity	NPC74410

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 NPC147066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1410
0.2-0.3	4157
0.3-0.4	2297
0.4-0.5	632
0.5-0.6	201
0.6-0.7	122
0.7-0.8	132
0.8-0.85	35
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD4786	Approved
0.8875	High Similarity	NPD4223	Phase 3
0.8875	High Similarity	NPD4221	Approved
0.878	High Similarity	NPD5329	Approved
0.8721	High Similarity	NPD6399	Phase 3
0.8675	High Similarity	NPD6098	Approved
0.8659	High Similarity	NPD4197	Approved
0.8642	High Similarity	NPD3667	Approved
0.8471	Intermediate Similarity	NPD5737	Approved
0.8471	Intermediate Similarity	NPD6672	Approved
0.8452	Intermediate Similarity	NPD4689	Approved
0.8452	Intermediate Similarity	NPD7334	Approved
0.8452	Intermediate Similarity	NPD4690	Approved
0.8452	Intermediate Similarity	NPD5205	Approved
0.8452	Intermediate Similarity	NPD7146	Approved
0.8452	Intermediate Similarity	NPD4138	Approved
0.8452	Intermediate Similarity	NPD5330	Approved
0.8452	Intermediate Similarity	NPD6409	Approved
0.8452	Intermediate Similarity	NPD7521	Approved
0.8452	Intermediate Similarity	NPD4688	Approved
0.8452	Intermediate Similarity	NPD4693	Phase 3
0.8452	Intermediate Similarity	NPD6684	Approved
0.8434	Intermediate Similarity	NPD3133	Approved
0.8434	Intermediate Similarity	NPD3665	Phase 1
0.8434	Intermediate Similarity	NPD3666	Approved
0.8391	Intermediate Similarity	NPD5281	Approved
0.8391	Intermediate Similarity	NPD5284	Approved
0.8375	Intermediate Similarity	NPD3617	Approved
0.8372	Intermediate Similarity	NPD6673	Approved
0.8372	Intermediate Similarity	NPD6080	Approved
0.8372	Intermediate Similarity	NPD6904	Approved
0.8372	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD6084	Phase 2
0.8333	Intermediate Similarity	NPD6083	Phase 2
0.8256	Intermediate Similarity	NPD5208	Approved
0.8256	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6903	Approved
0.8235	Intermediate Similarity	NPD4694	Approved
0.8235	Intermediate Similarity	NPD5280	Approved
0.8235	Intermediate Similarity	NPD5690	Phase 2
0.8235	Intermediate Similarity	NPD3618	Phase 1
0.8182	Intermediate Similarity	NPD6079	Approved
0.8182	Intermediate Similarity	NPD4747	Approved
0.8161	Intermediate Similarity	NPD4753	Phase 2
0.8118	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD5695	Phase 3
0.8077	Intermediate Similarity	NPD4243	Approved
0.8072	Intermediate Similarity	NPD4692	Approved
0.8072	Intermediate Similarity	NPD4139	Approved
0.8052	Intermediate Similarity	NPD4137	Phase 3
0.8049	Intermediate Similarity	NPD4195	Approved
0.8043	Intermediate Similarity	NPD5696	Approved
0.8023	Intermediate Similarity	NPD5279	Phase 3
0.8023	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3668	Phase 3
0.7978	Intermediate Similarity	NPD5693	Phase 1
0.7978	Intermediate Similarity	NPD7515	Phase 2
0.7978	Intermediate Similarity	NPD6050	Approved
0.7955	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4695	Discontinued
0.7949	Intermediate Similarity	NPD4691	Approved
0.7922	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4224	Phase 2
0.7889	Intermediate Similarity	NPD4202	Approved
0.7882	Intermediate Similarity	NPD4788	Approved
0.7875	Intermediate Similarity	NPD4785	Approved
0.7875	Intermediate Similarity	NPD4784	Approved
0.7875	Intermediate Similarity	NPD5733	Approved
0.7865	Intermediate Similarity	NPD5207	Approved
0.7865	Intermediate Similarity	NPD5692	Phase 3
0.7848	Intermediate Similarity	NPD6081	Approved
0.7816	Intermediate Similarity	NPD4519	Discontinued
0.7816	Intermediate Similarity	NPD4623	Approved
0.7802	Intermediate Similarity	NPD7748	Approved
0.7802	Intermediate Similarity	NPD6001	Approved
0.7778	Intermediate Similarity	NPD6942	Approved
0.7778	Intermediate Similarity	NPD5694	Approved
0.7778	Intermediate Similarity	NPD7339	Approved
0.7732	Intermediate Similarity	NPD6675	Approved
0.7732	Intermediate Similarity	NPD7128	Approved
0.7732	Intermediate Similarity	NPD6402	Approved
0.7732	Intermediate Similarity	NPD5739	Approved
0.7717	Intermediate Similarity	NPD5210	Approved
0.7717	Intermediate Similarity	NPD4629	Approved
0.7667	Intermediate Similarity	NPD4096	Approved
0.7654	Intermediate Similarity	NPD4058	Approved
0.7654	Intermediate Similarity	NPD4687	Approved
0.7634	Intermediate Similarity	NPD4697	Phase 3
0.7634	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5222	Approved
0.7634	Intermediate Similarity	NPD5221	Approved
0.7625	Intermediate Similarity	NPD5276	Approved
0.7582	Intermediate Similarity	NPD8035	Phase 2
0.7582	Intermediate Similarity	NPD8034	Phase 2
0.7579	Intermediate Similarity	NPD6404	Discontinued
0.7576	Intermediate Similarity	NPD6881	Approved
0.7576	Intermediate Similarity	NPD7320	Approved
0.7576	Intermediate Similarity	NPD6899	Approved
0.7561	Intermediate Similarity	NPD4190	Phase 3
0.7561	Intermediate Similarity	NPD5275	Approved
0.7553	Intermediate Similarity	NPD4755	Approved
0.7553	Intermediate Similarity	NPD7902	Approved
0.7553	Intermediate Similarity	NPD5173	Approved
0.7528	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5133	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6372	Approved
0.7475	Intermediate Similarity	NPD5701	Approved
0.7475	Intermediate Similarity	NPD5697	Approved
0.747	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5360	Phase 3
0.7468	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7614	Phase 1
0.7444	Intermediate Similarity	NPD4518	Approved
0.7439	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7290	Approved
0.7426	Intermediate Similarity	NPD7102	Approved
0.7426	Intermediate Similarity	NPD6883	Approved
0.74	Intermediate Similarity	NPD6011	Approved
0.7396	Intermediate Similarity	NPD4700	Approved
0.7396	Intermediate Similarity	NPD4696	Approved
0.7396	Intermediate Similarity	NPD5285	Approved
0.7396	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD8130	Phase 1
0.7353	Intermediate Similarity	NPD6617	Approved
0.7353	Intermediate Similarity	NPD6869	Approved
0.7353	Intermediate Similarity	NPD6650	Approved
0.7353	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6649	Approved
0.7353	Intermediate Similarity	NPD6847	Approved
0.7347	Intermediate Similarity	NPD6052	Approved
0.734	Intermediate Similarity	NPD5654	Approved
0.7327	Intermediate Similarity	NPD6012	Approved
0.7327	Intermediate Similarity	NPD6013	Approved
0.7327	Intermediate Similarity	NPD6014	Approved
0.7326	Intermediate Similarity	NPD7525	Registered
0.732	Intermediate Similarity	NPD5223	Approved
0.7308	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7638	Approved
0.7284	Intermediate Similarity	NPD4789	Approved
0.7282	Intermediate Similarity	NPD6882	Approved
0.7282	Intermediate Similarity	NPD8297	Approved
0.7262	Intermediate Similarity	NPD6117	Approved
0.7245	Intermediate Similarity	NPD5226	Approved
0.7245	Intermediate Similarity	NPD5224	Approved
0.7245	Intermediate Similarity	NPD5211	Phase 2
0.7245	Intermediate Similarity	NPD4633	Approved
0.7245	Intermediate Similarity	NPD5225	Approved
0.7245	Intermediate Similarity	NPD5091	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6926	Approved
0.7229	Intermediate Similarity	NPD6924	Approved
0.7216	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD7640	Approved
0.7195	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5959	Approved
0.7176	Intermediate Similarity	NPD6116	Phase 1
0.7174	Intermediate Similarity	NPD6051	Approved
0.7172	Intermediate Similarity	NPD5174	Approved
0.7172	Intermediate Similarity	NPD4754	Approved
0.7172	Intermediate Similarity	NPD5175	Approved
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3702	Approved
0.7129	Intermediate Similarity	NPD6412	Phase 2
0.7129	Intermediate Similarity	NPD6614	Approved
0.71	Intermediate Similarity	NPD5141	Approved
0.7093	Intermediate Similarity	NPD6115	Approved
0.7093	Intermediate Similarity	NPD6118	Approved
0.7093	Intermediate Similarity	NPD6114	Approved
0.7093	Intermediate Similarity	NPD6697	Approved
0.7075	Intermediate Similarity	NPD6868	Approved
0.7073	Intermediate Similarity	NPD4245	Approved
0.7073	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD6933	Approved
0.7048	Intermediate Similarity	NPD4632	Approved
0.703	Intermediate Similarity	NPD4768	Approved
0.703	Intermediate Similarity	NPD6008	Approved
0.703	Intermediate Similarity	NPD4767	Approved
0.7021	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6988	Remote Similarity	NPD4758	Discontinued
0.6988	Remote Similarity	NPD5777	Approved
0.6951	Remote Similarity	NPD6922	Approved
0.6951	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6923	Approved
0.6951	Remote Similarity	NPD3698	Phase 2
0.6944	Remote Similarity	NPD6335	Approved
0.6932	Remote Similarity	NPD5368	Approved
0.6916	Remote Similarity	NPD6274	Approved
0.6907	Remote Similarity	NPD7732	Phase 3
0.6893	Remote Similarity	NPD5128	Approved
0.6893	Remote Similarity	NPD4730	Approved
0.6893	Remote Similarity	NPD4729	Approved
0.6893	Remote Similarity	NPD5168	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