NPASS Compound

Structure

CID301244 OpenBabel06191716112D 33 37 0 0 1 0 0 0 0 0999 V2000 -4.4682 -0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9887 1.0796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5034 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 -0.6173 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 -0.0000 0.9737 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 -0.8432 -1.4605 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 -2.9211 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 0.8432 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 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 -3.3729 1.9474 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 -3.3729 -0.0000 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 -2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 2 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 -4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -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 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 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 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 28 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	6.201
LogD:	4.858
LogS:	-5.168
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	4.802
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.45
MDCK Permeability:	1.7389795175404288e-05
Pgp-inhibitor:	0.146
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	93.9698715209961%
Volume Distribution (VD):	0.721
Pgp-substrate:	4.815665245056152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.332
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	1.741
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.595
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.04
Carcinogencity:	0.033
Eye Corrosion:	0.011
Eye Irritation:	0.037
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC301244

Natural Product ID:	NPC301244
*Common Name:**	3Alphahydroxyolean-11,13(18)-Dien-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10R,12aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12-dodecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	XMOMYSSKYVFTKO-LNVXMQETSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8-9,21-23,31H,10-18H2,1-7H3,(H,32,33)/t21-,22+,23+,27-,28+,29+,30-/m0/s1
SMILES:	O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C=CC2=C3CC(C)(C)CC[C@@]3(CC[C@@]12C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486582
PubChem CID:	10766159
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
NPO32595	junellia tridens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141098]
NPO23200	Fatsia polycarpa	Species	Araliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21766884]
NPO23200	Fatsia polycarpa	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21766884]
NPO23200	Fatsia polycarpa	Species	Araliaceae	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	2
MIC	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[573186]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	64.0	ug.mL-1	PMID[573185]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	128.0	ug.mL-1	PMID[573186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[573186]

☑ 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 NPC301244 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	201
0.1-0.2	1035
0.2-0.3	4244
0.3-0.4	12243
0.4-0.5	11592
0.5-0.6	6056
0.6-0.7	4981
0.7-0.8	1884
0.8-0.85	250
0.85-0.9	159
0.9-0.95	49
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC80365
0.9535	High Similarity	NPC474686
0.9535	High Similarity	NPC474972
0.9535	High Similarity	NPC95246
0.9535	High Similarity	NPC161751
0.9529	High Similarity	NPC71507
0.9444	High Similarity	NPC21728
0.9419	High Similarity	NPC290690
0.9419	High Similarity	NPC470629
0.9419	High Similarity	NPC17733
0.9419	High Similarity	NPC474512
0.9419	High Similarity	NPC181225
0.9419	High Similarity	NPC473242
0.9333	High Similarity	NPC9487
0.931	High Similarity	NPC143232
0.931	High Similarity	NPC470588
0.931	High Similarity	NPC274330
0.931	High Similarity	NPC198664
0.9302	High Similarity	NPC242468
0.9302	High Similarity	NPC171203
0.9302	High Similarity	NPC18064
0.9302	High Similarity	NPC68160
0.9302	High Similarity	NPC98442
0.9302	High Similarity	NPC88716
0.9302	High Similarity	NPC293564
0.9302	High Similarity	NPC142415
0.9302	High Similarity	NPC130577
0.9302	High Similarity	NPC102683
0.9302	High Similarity	NPC51700
0.9302	High Similarity	NPC307426
0.9213	High Similarity	NPC133579
0.9213	High Similarity	NPC474806
0.9205	High Similarity	NPC126369
0.9205	High Similarity	NPC470589
0.9205	High Similarity	NPC111110
0.9195	High Similarity	NPC40552
0.9195	High Similarity	NPC246708
0.9195	High Similarity	NPC182797
0.9195	High Similarity	NPC52169
0.9186	High Similarity	NPC72638
0.9176	High Similarity	NPC171789
0.9121	High Similarity	NPC88847
0.9101	High Similarity	NPC187722
0.9091	High Similarity	NPC25906
0.9091	High Similarity	NPC59263
0.9091	High Similarity	NPC293048
0.9091	High Similarity	NPC130520
0.9091	High Similarity	NPC234346
0.9091	High Similarity	NPC290972
0.9091	High Similarity	NPC270768
0.9091	High Similarity	NPC121798
0.9091	High Similarity	NPC263393
0.9091	High Similarity	NPC61543
0.9091	High Similarity	NPC225585
0.9091	High Similarity	NPC127689
0.9091	High Similarity	NPC64872
0.9011	High Similarity	NPC32118
0.9	High Similarity	NPC202728
0.9	High Similarity	NPC229281
0.9	High Similarity	NPC158059
0.9	High Similarity	NPC118519
0.8989	High Similarity	NPC130278
0.8989	High Similarity	NPC273621
0.8989	High Similarity	NPC477872
0.8989	High Similarity	NPC474728
0.8989	High Similarity	NPC86372
0.8989	High Similarity	NPC210037
0.8989	High Similarity	NPC172361
0.8989	High Similarity	NPC291028
0.8989	High Similarity	NPC7260
0.8989	High Similarity	NPC120968
0.8989	High Similarity	NPC18872
0.8989	High Similarity	NPC227467
0.8989	High Similarity	NPC290614
0.8966	High Similarity	NPC56588
0.8941	High Similarity	NPC73882
0.8901	High Similarity	NPC191412
0.8901	High Similarity	NPC114159
0.8901	High Similarity	NPC209868
0.8901	High Similarity	NPC6818
0.8901	High Similarity	NPC159365
0.8889	High Similarity	NPC145067
0.8889	High Similarity	NPC300351
0.8889	High Similarity	NPC60755
0.8889	High Similarity	NPC77099
0.8889	High Similarity	NPC324341
0.8889	High Similarity	NPC65120
0.8889	High Similarity	NPC285184
0.8889	High Similarity	NPC235884
0.8889	High Similarity	NPC474525
0.8889	High Similarity	NPC966
0.8889	High Similarity	NPC282616
0.8889	High Similarity	NPC155120
0.8889	High Similarity	NPC470590
0.8889	High Similarity	NPC52021
0.8889	High Similarity	NPC105189
0.8889	High Similarity	NPC472149
0.8889	High Similarity	NPC158030
0.8889	High Similarity	NPC288833
0.8889	High Similarity	NPC228784
0.8889	High Similarity	NPC84319
0.8889	High Similarity	NPC38754
0.8889	High Similarity	NPC306541
0.8889	High Similarity	NPC25299
0.8889	High Similarity	NPC71074
0.8889	High Similarity	NPC4036
0.8889	High Similarity	NPC233455
0.8876	High Similarity	NPC102414
0.8876	High Similarity	NPC77168
0.8876	High Similarity	NPC84271
0.8864	High Similarity	NPC73064
0.8851	High Similarity	NPC133954
0.8824	High Similarity	NPC473420
0.8804	High Similarity	NPC96916
0.8804	High Similarity	NPC198245
0.8804	High Similarity	NPC473240
0.8791	High Similarity	NPC86368
0.8791	High Similarity	NPC63118
0.8791	High Similarity	NPC474436
0.8791	High Similarity	NPC295643
0.8791	High Similarity	NPC74855
0.8791	High Similarity	NPC307335
0.8791	High Similarity	NPC214756
0.8791	High Similarity	NPC298554
0.8791	High Similarity	NPC275809
0.8791	High Similarity	NPC136313
0.8791	High Similarity	NPC272075
0.8791	High Similarity	NPC49776
0.8778	High Similarity	NPC120840
0.8778	High Similarity	NPC113989
0.8778	High Similarity	NPC49320
0.8778	High Similarity	NPC46441
0.8778	High Similarity	NPC193750
0.875	High Similarity	NPC325594
0.875	High Similarity	NPC82979
0.875	High Similarity	NPC95594
0.875	High Similarity	NPC475862
0.875	High Similarity	NPC74363
0.875	High Similarity	NPC213412
0.875	High Similarity	NPC235341
0.875	High Similarity	NPC477579
0.875	High Similarity	NPC73038
0.8736	High Similarity	NPC180834
0.871	High Similarity	NPC157113
0.871	High Similarity	NPC259733
0.871	High Similarity	NPC204961
0.871	High Similarity	NPC476327
0.871	High Similarity	NPC73004
0.871	High Similarity	NPC116457
0.871	High Similarity	NPC173744
0.871	High Similarity	NPC132824
0.871	High Similarity	NPC158371
0.871	High Similarity	NPC207922
0.871	High Similarity	NPC476318
0.871	High Similarity	NPC327179
0.871	High Similarity	NPC62516
0.8696	High Similarity	NPC87095
0.8696	High Similarity	NPC188102
0.8696	High Similarity	NPC88116
0.8696	High Similarity	NPC222047
0.8696	High Similarity	NPC231063
0.8696	High Similarity	NPC145667
0.8696	High Similarity	NPC263548
0.8696	High Similarity	NPC282395
0.8696	High Similarity	NPC91010
0.8696	High Similarity	NPC474529
0.8696	High Similarity	NPC299996
0.8696	High Similarity	NPC32407
0.8696	High Similarity	NPC20235
0.8696	High Similarity	NPC60692
0.8681	High Similarity	NPC471588
0.8681	High Similarity	NPC235704
0.8681	High Similarity	NPC6255
0.8681	High Similarity	NPC475708
0.8667	High Similarity	NPC475049
0.8667	High Similarity	NPC30522
0.8652	High Similarity	NPC187376
0.8652	High Similarity	NPC474684
0.8652	High Similarity	NPC142361
0.8652	High Similarity	NPC159046
0.8652	High Similarity	NPC233836
0.8621	High Similarity	NPC70834
0.8621	High Similarity	NPC312480
0.8621	High Similarity	NPC82538
0.8621	High Similarity	NPC237795
0.8617	High Similarity	NPC247139
0.8617	High Similarity	NPC187933
0.8617	High Similarity	NPC259788
0.8617	High Similarity	NPC43686
0.8617	High Similarity	NPC9613
0.8617	High Similarity	NPC189880
0.8617	High Similarity	NPC255589
0.8605	High Similarity	NPC142244
0.8602	High Similarity	NPC148523
0.8602	High Similarity	NPC474727
0.8602	High Similarity	NPC139570
0.8602	High Similarity	NPC83693
0.8602	High Similarity	NPC290481
0.8602	High Similarity	NPC195715
0.8587	High Similarity	NPC118490

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 NPC301244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1293
0.2-0.3	3596
0.3-0.4	2605
0.4-0.5	930
0.5-0.6	265
0.6-0.7	220
0.7-0.8	55
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7515	Phase 2
0.8495	Intermediate Similarity	NPD7748	Approved
0.8261	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7902	Approved
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD4786	Approved
0.809	Intermediate Similarity	NPD3667	Approved
0.8085	Intermediate Similarity	NPD6411	Approved
0.7955	Intermediate Similarity	NPD7645	Phase 2
0.7935	Intermediate Similarity	NPD3618	Phase 1
0.7917	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7900	Approved
0.7895	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD6101	Approved
0.7872	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5328	Approved
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.7579	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5279	Phase 3
0.7527	Intermediate Similarity	NPD3666	Approved
0.7527	Intermediate Similarity	NPD3665	Phase 1
0.7527	Intermediate Similarity	NPD3133	Approved
0.7526	Intermediate Similarity	NPD8034	Phase 2
0.7526	Intermediate Similarity	NPD8035	Phase 2
0.7474	Intermediate Similarity	NPD3573	Approved
0.7449	Intermediate Similarity	NPD5779	Approved
0.7449	Intermediate Similarity	NPD4202	Approved
0.7449	Intermediate Similarity	NPD5778	Approved
0.7426	Intermediate Similarity	NPD7638	Approved
0.74	Intermediate Similarity	NPD5221	Approved
0.74	Intermediate Similarity	NPD5222	Approved
0.74	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD6899	Approved
0.7358	Intermediate Similarity	NPD6881	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD5284	Approved
0.7347	Intermediate Similarity	NPD5281	Approved
0.734	Intermediate Similarity	NPD3668	Phase 3
0.7333	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD6675	Approved
0.7333	Intermediate Similarity	NPD6402	Approved
0.7327	Intermediate Similarity	NPD5173	Approved
0.7303	Intermediate Similarity	NPD7339	Approved
0.7303	Intermediate Similarity	NPD8264	Approved
0.7303	Intermediate Similarity	NPD6942	Approved
0.7283	Intermediate Similarity	NPD7525	Registered
0.7283	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5697	Approved
0.7228	Intermediate Similarity	NPD7614	Phase 1
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7222	Intermediate Similarity	NPD6883	Approved
0.7222	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6117	Approved
0.7222	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD7290	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7196	Intermediate Similarity	NPD7320	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5286	Approved
0.7184	Intermediate Similarity	NPD5285	Approved
0.7184	Intermediate Similarity	NPD4696	Approved
0.7157	Intermediate Similarity	NPD6083	Phase 2
0.7157	Intermediate Similarity	NPD4755	Approved
0.7157	Intermediate Similarity	NPD6084	Phase 2
0.7156	Intermediate Similarity	NPD8130	Phase 1
0.7156	Intermediate Similarity	NPD6650	Approved
0.7156	Intermediate Similarity	NPD6617	Approved
0.7156	Intermediate Similarity	NPD6869	Approved
0.7156	Intermediate Similarity	NPD6649	Approved
0.7156	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD5223	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7091	Intermediate Similarity	NPD8297	Approved
0.7091	Intermediate Similarity	NPD6882	Approved
0.7065	Intermediate Similarity	NPD6115	Approved
0.7065	Intermediate Similarity	NPD6697	Approved
0.7065	Intermediate Similarity	NPD6118	Approved
0.7065	Intermediate Similarity	NPD6114	Approved
0.7048	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD5226	Approved
0.7048	Intermediate Similarity	NPD5224	Approved
0.7048	Intermediate Similarity	NPD5211	Phase 2
0.7048	Intermediate Similarity	NPD5225	Approved
0.7041	Intermediate Similarity	NPD6672	Approved
0.7041	Intermediate Similarity	NPD5737	Approved
0.7019	Intermediate Similarity	NPD4700	Approved
0.701	Intermediate Similarity	NPD5280	Approved
0.701	Intermediate Similarity	NPD4694	Approved
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6926	Approved
0.6981	Remote Similarity	NPD5175	Approved
0.6981	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD7152	Approved
0.6966	Remote Similarity	NPD7151	Approved
0.6966	Remote Similarity	NPD7150	Approved
0.6961	Remote Similarity	NPD5695	Phase 3
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6916	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD5329	Approved
0.6903	Remote Similarity	NPD6868	Approved
0.69	Remote Similarity	NPD5207	Approved
0.6893	Remote Similarity	NPD7732	Phase 3
0.6875	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD4788	Approved
0.6854	Remote Similarity	NPD7143	Approved
0.6854	Remote Similarity	NPD7144	Approved
0.6848	Remote Similarity	NPD6933	Approved
0.6842	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4623	Approved
0.6837	Remote Similarity	NPD6098	Approved
0.6837	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5690	Phase 2
0.6832	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD5694	Approved
0.6832	Remote Similarity	NPD7637	Suspended
0.6822	Remote Similarity	NPD4754	Approved
0.6804	Remote Similarity	NPD4197	Approved
0.6796	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD4629	Approved
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6335	Approved
0.678	Remote Similarity	NPD8328	Phase 3
0.6778	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5696	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6742	Remote Similarity	NPD6922	Approved
0.6742	Remote Similarity	NPD6923	Approved
0.6742	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8039	Approved
0.6737	Remote Similarity	NPD7509	Discontinued
0.6735	Remote Similarity	NPD1694	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.6729	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD4730	Approved
0.6727	Remote Similarity	NPD5168	Approved
0.6727	Remote Similarity	NPD4729	Approved
0.6724	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7101	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4518	Approved
0.6698	Remote Similarity	NPD6404	Discontinued
0.6697	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD4767	Approved
0.6697	Remote Similarity	NPD4768	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6632	Remote Similarity	NPD6929	Approved
0.663	Remote Similarity	NPD4687	Approved
0.663	Remote Similarity	NPD4785	Approved
0.663	Remote Similarity	NPD4784	Approved
0.663	Remote Similarity	NPD5733	Approved
0.663	Remote Similarity	NPD4058	Approved
0.6609	Remote Similarity	NPD6274	Approved
0.6607	Remote Similarity	NPD5251	Approved
0.6607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5250	Approved
0.6607	Remote Similarity	NPD5249	Phase 3
0.6607	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD5247	Approved
0.6607	Remote Similarity	NPD5248	Approved
0.6607	Remote Similarity	NPD5135	Approved
0.6607	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD4752	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