NPASS Compound

Structure

NPC474684 OpenBabel07101718192D 33 36 0 0 1 0 0 0 0 0999 V2000 4.8126 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 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 6 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 31 1 1 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	7.209
LogD:	5.185
LogS:	-4.489
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.717
Fsp3:	0.833
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:	-5.197
MDCK Permeability:	1.1347025974828284e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	94.59575653076172%
Volume Distribution (VD):	0.768
Pgp-substrate:	2.6440320014953613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	9.105
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.416
Carcinogencity:	0.131
Eye Corrosion:	0.011
Eye Irritation:	0.052
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC474684

Natural Product ID:	NPC474684
*Common Name:**	3-Beta-Hydroxytirucalla-7,24-Dien-21-Oic Acid
IUPAC Name:	(2S)-2-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	CGPBVNAIDFBRJG-ZRMZZLDZSA-N
Standard InCHI:	InChI=1S/C30H48O3/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/h9,11,20-22,24-25,31H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,25-,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)CC[C@@H](C2(C)C)O)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479306
PubChem CID:	10695137
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]

☑ 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	=	100.0	ug.mL-1	PMID[551330]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	50.0	%	PMID[551330]

☑ 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 NPC474684 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	162
0.1-0.2	1040
0.2-0.3	4798
0.3-0.4	14935
0.4-0.5	7452
0.5-0.6	5663
0.6-0.7	4904
0.7-0.8	2925
0.8-0.85	625
0.85-0.9	161
0.9-0.95	26
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142361
0.9759	High Similarity	NPC474704
0.9759	High Similarity	NPC475921
0.9756	High Similarity	NPC187376
0.9756	High Similarity	NPC159046
0.9756	High Similarity	NPC233836
0.9634	High Similarity	NPC155011
0.9634	High Similarity	NPC28252
0.9634	High Similarity	NPC55309
0.9529	High Similarity	NPC189520
0.9524	High Similarity	NPC84271
0.9524	High Similarity	NPC102414
0.9524	High Similarity	NPC77168
0.9419	High Similarity	NPC470224
0.9419	High Similarity	NPC470375
0.9419	High Similarity	NPC470376
0.9412	High Similarity	NPC471896
0.9405	High Similarity	NPC242864
0.9302	High Similarity	NPC110657
0.9302	High Similarity	NPC212301
0.9302	High Similarity	NPC86266
0.9294	High Similarity	NPC128496
0.9195	High Similarity	NPC107674
0.9195	High Similarity	NPC170220
0.9195	High Similarity	NPC141497
0.9195	High Similarity	NPC477855
0.9186	High Similarity	NPC111585
0.9186	High Similarity	NPC175628
0.9186	High Similarity	NPC148414
0.9186	High Similarity	NPC469400
0.9167	High Similarity	NPC325594
0.9167	High Similarity	NPC73038
0.9167	High Similarity	NPC94755
0.9157	High Similarity	NPC165064
0.9157	High Similarity	NPC221758
0.9157	High Similarity	NPC59453
0.9091	High Similarity	NPC469406
0.9091	High Similarity	NPC49670
0.908	High Similarity	NPC297265
0.908	High Similarity	NPC23434
0.908	High Similarity	NPC26888
0.907	High Similarity	NPC474889
0.9059	High Similarity	NPC307426
0.9059	High Similarity	NPC130577
0.9059	High Similarity	NPC51700
0.9059	High Similarity	NPC475740
0.9059	High Similarity	NPC102683
0.9059	High Similarity	NPC88716
0.9059	High Similarity	NPC68160
0.9059	High Similarity	NPC293564
0.9059	High Similarity	NPC142415
0.9059	High Similarity	NPC242468
0.9059	High Similarity	NPC18064
0.9059	High Similarity	NPC96496
0.9059	High Similarity	NPC98442
0.9059	High Similarity	NPC171203
0.9048	High Similarity	NPC294438
0.9048	High Similarity	NPC470574
0.9048	High Similarity	NPC264317
0.9024	High Similarity	NPC147066
0.9024	High Similarity	NPC473420
0.9	High Similarity	NPC108078
0.8989	High Similarity	NPC162001
0.8989	High Similarity	NPC279974
0.8989	High Similarity	NPC222845
0.8989	High Similarity	NPC45324
0.8953	High Similarity	NPC246708
0.8953	High Similarity	NPC52169
0.8953	High Similarity	NPC193360
0.8953	High Similarity	NPC470629
0.8953	High Similarity	NPC290690
0.8953	High Similarity	NPC473242
0.8953	High Similarity	NPC182797
0.8953	High Similarity	NPC17733
0.8953	High Similarity	NPC471722
0.8953	High Similarity	NPC328539
0.8953	High Similarity	NPC40552
0.8953	High Similarity	NPC474512
0.8953	High Similarity	NPC181225
0.8941	High Similarity	NPC474733
0.8941	High Similarity	NPC474970
0.8941	High Similarity	NPC2783
0.8941	High Similarity	NPC51014
0.8941	High Similarity	NPC12774
0.8941	High Similarity	NPC474732
0.8941	High Similarity	NPC72638
0.8941	High Similarity	NPC145879
0.8941	High Similarity	NPC72133
0.8941	High Similarity	NPC31564
0.8941	High Similarity	NPC474778
0.8929	High Similarity	NPC214043
0.8929	High Similarity	NPC85774
0.8929	High Similarity	NPC82902
0.8916	High Similarity	NPC151519
0.8889	High Similarity	NPC173272
0.8876	High Similarity	NPC166906
0.8876	High Similarity	NPC159410
0.8864	High Similarity	NPC272746
0.8864	High Similarity	NPC154101
0.8851	High Similarity	NPC25906
0.8851	High Similarity	NPC59263
0.8851	High Similarity	NPC473999
0.8851	High Similarity	NPC61543
0.8851	High Similarity	NPC275740
0.8851	High Similarity	NPC1015
0.8851	High Similarity	NPC225585
0.8851	High Similarity	NPC234346
0.8851	High Similarity	NPC64872
0.8851	High Similarity	NPC262858
0.8851	High Similarity	NPC143232
0.8851	High Similarity	NPC263393
0.8851	High Similarity	NPC198664
0.8851	High Similarity	NPC270768
0.8851	High Similarity	NPC472240
0.8851	High Similarity	NPC31985
0.8851	High Similarity	NPC309603
0.8851	High Similarity	NPC274330
0.8851	High Similarity	NPC86319
0.8851	High Similarity	NPC121798
0.8851	High Similarity	NPC474972
0.8851	High Similarity	NPC161751
0.8851	High Similarity	NPC130520
0.8851	High Similarity	NPC32830
0.8851	High Similarity	NPC293048
0.8851	High Similarity	NPC95246
0.8851	High Similarity	NPC474245
0.8851	High Similarity	NPC127689
0.8851	High Similarity	NPC470588
0.8851	High Similarity	NPC290972
0.8837	High Similarity	NPC264005
0.8837	High Similarity	NPC269360
0.8837	High Similarity	NPC71507
0.8837	High Similarity	NPC33768
0.8837	High Similarity	NPC58063
0.8824	High Similarity	NPC471224
0.8824	High Similarity	NPC474218
0.8795	High Similarity	NPC201912
0.8795	High Similarity	NPC38350
0.878	High Similarity	NPC477371
0.8778	High Similarity	NPC470016
0.8778	High Similarity	NPC317586
0.8778	High Similarity	NPC469599
0.8778	High Similarity	NPC69548
0.8778	High Similarity	NPC48330
0.8778	High Similarity	NPC184848
0.8764	High Similarity	NPC63118
0.8764	High Similarity	NPC475255
0.8764	High Similarity	NPC49776
0.8764	High Similarity	NPC474436
0.875	High Similarity	NPC44240
0.875	High Similarity	NPC85173
0.875	High Similarity	NPC126369
0.875	High Similarity	NPC126993
0.875	High Similarity	NPC172361
0.875	High Similarity	NPC111110
0.875	High Similarity	NPC20388
0.875	High Similarity	NPC130278
0.875	High Similarity	NPC7260
0.875	High Similarity	NPC210037
0.875	High Similarity	NPC86372
0.875	High Similarity	NPC470589
0.875	High Similarity	NPC290614
0.875	High Similarity	NPC477872
0.875	High Similarity	NPC48010
0.875	High Similarity	NPC291028
0.875	High Similarity	NPC273621
0.875	High Similarity	NPC227467
0.875	High Similarity	NPC120968
0.875	High Similarity	NPC191684
0.875	High Similarity	NPC18872
0.8736	High Similarity	NPC474719
0.8736	High Similarity	NPC53911
0.8736	High Similarity	NPC16377
0.8736	High Similarity	NPC131470
0.8736	High Similarity	NPC471724
0.8736	High Similarity	NPC146937
0.8736	High Similarity	NPC143767
0.8736	High Similarity	NPC328313
0.8736	High Similarity	NPC471900
0.8721	High Similarity	NPC469994
0.8721	High Similarity	NPC82979
0.8721	High Similarity	NPC264127
0.8706	High Similarity	NPC476038
0.8706	High Similarity	NPC171789
0.8706	High Similarity	NPC194937
0.8706	High Similarity	NPC473246
0.8696	High Similarity	NPC477813
0.8696	High Similarity	NPC48647
0.8696	High Similarity	NPC119036
0.8696	High Similarity	NPC186810
0.8696	High Similarity	NPC114274
0.8696	High Similarity	NPC477854
0.869	High Similarity	NPC260956
0.869	High Similarity	NPC320514
0.869	High Similarity	NPC73882
0.869	High Similarity	NPC48362
0.8681	High Similarity	NPC96859
0.8681	High Similarity	NPC328162
0.8681	High Similarity	NPC120708
0.8681	High Similarity	NPC327788

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 NPC474684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1363
0.2-0.3	3990
0.3-0.4	2483
0.4-0.5	637
0.5-0.6	193
0.6-0.7	118
0.7-0.8	155
0.8-0.85	58
0.85-0.9	7
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9157	High Similarity	NPD4786	Approved
0.907	High Similarity	NPD5328	Approved
0.9048	High Similarity	NPD7520	Clinical (unspecified phase)
0.8941	High Similarity	NPD3618	Phase 1
0.8916	High Similarity	NPD3667	Approved
0.8864	High Similarity	NPD6079	Approved
0.8764	High Similarity	NPD6399	Phase 3
0.8652	High Similarity	NPD7515	Phase 2
0.8556	High Similarity	NPD4202	Approved
0.8488	Intermediate Similarity	NPD3133	Approved
0.8488	Intermediate Similarity	NPD3665	Phase 1
0.8488	Intermediate Similarity	NPD3666	Approved
0.8351	Intermediate Similarity	NPD6402	Approved
0.8351	Intermediate Similarity	NPD7128	Approved
0.8351	Intermediate Similarity	NPD5739	Approved
0.8351	Intermediate Similarity	NPD6675	Approved
0.8295	Intermediate Similarity	NPD7334	Approved
0.8295	Intermediate Similarity	NPD6409	Approved
0.8295	Intermediate Similarity	NPD6684	Approved
0.8295	Intermediate Similarity	NPD7521	Approved
0.8295	Intermediate Similarity	NPD7146	Approved
0.8295	Intermediate Similarity	NPD5330	Approved
0.8293	Intermediate Similarity	NPD6942	Approved
0.8293	Intermediate Similarity	NPD7339	Approved
0.828	Intermediate Similarity	NPD4697	Phase 3
0.828	Intermediate Similarity	NPD5221	Approved
0.828	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5222	Approved
0.8261	Intermediate Similarity	NPD7748	Approved
0.8242	Intermediate Similarity	NPD8034	Phase 2
0.8242	Intermediate Similarity	NPD8035	Phase 2
0.8235	Intermediate Similarity	NPD7525	Registered
0.8193	Intermediate Similarity	NPD6117	Approved
0.8191	Intermediate Similarity	NPD6084	Phase 2
0.8191	Intermediate Similarity	NPD6083	Phase 2
0.8191	Intermediate Similarity	NPD4755	Approved
0.8191	Intermediate Similarity	NPD5173	Approved
0.8182	Intermediate Similarity	NPD6899	Approved
0.8182	Intermediate Similarity	NPD6881	Approved
0.8182	Intermediate Similarity	NPD7320	Approved
0.8171	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6903	Approved
0.8111	Intermediate Similarity	NPD5737	Approved
0.8111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6672	Approved
0.8105	Intermediate Similarity	NPD7638	Approved
0.81	Intermediate Similarity	NPD6373	Approved
0.81	Intermediate Similarity	NPD6372	Approved
0.8095	Intermediate Similarity	NPD6116	Phase 1
0.809	Intermediate Similarity	NPD5279	Phase 3
0.8081	Intermediate Similarity	NPD5701	Approved
0.8081	Intermediate Similarity	NPD5697	Approved
0.8068	Intermediate Similarity	NPD3668	Phase 3
0.8046	Intermediate Similarity	NPD4223	Phase 3
0.8046	Intermediate Similarity	NPD4221	Approved
0.8022	Intermediate Similarity	NPD4753	Phase 2
0.8021	Intermediate Similarity	NPD4700	Approved
0.8021	Intermediate Similarity	NPD4696	Approved
0.8021	Intermediate Similarity	NPD5285	Approved
0.8021	Intermediate Similarity	NPD7640	Approved
0.8021	Intermediate Similarity	NPD5286	Approved
0.8021	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD7102	Approved
0.802	Intermediate Similarity	NPD7290	Approved
0.802	Intermediate Similarity	NPD6883	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6114	Approved
0.8	Intermediate Similarity	NPD6697	Approved
0.8	Intermediate Similarity	NPD6115	Approved
0.8	Intermediate Similarity	NPD6118	Approved
0.7978	Intermediate Similarity	NPD5329	Approved
0.7976	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6869	Approved
0.7941	Intermediate Similarity	NPD6649	Approved
0.7941	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6847	Approved
0.7941	Intermediate Similarity	NPD6650	Approved
0.7941	Intermediate Similarity	NPD8130	Phase 1
0.7941	Intermediate Similarity	NPD6617	Approved
0.7938	Intermediate Similarity	NPD5223	Approved
0.7921	Intermediate Similarity	NPD6014	Approved
0.7921	Intermediate Similarity	NPD6013	Approved
0.7921	Intermediate Similarity	NPD6012	Approved
0.7889	Intermediate Similarity	NPD6098	Approved
0.7865	Intermediate Similarity	NPD4197	Approved
0.7864	Intermediate Similarity	NPD6882	Approved
0.7864	Intermediate Similarity	NPD8297	Approved
0.7857	Intermediate Similarity	NPD5224	Approved
0.7857	Intermediate Similarity	NPD5226	Approved
0.7857	Intermediate Similarity	NPD5225	Approved
0.7857	Intermediate Similarity	NPD4633	Approved
0.7857	Intermediate Similarity	NPD5211	Phase 2
0.7789	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD4754	Approved
0.7778	Intermediate Similarity	NPD5175	Approved
0.7753	Intermediate Similarity	NPD4788	Approved
0.7732	Intermediate Similarity	NPD5696	Approved
0.7711	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7645	Phase 2
0.77	Intermediate Similarity	NPD5141	Approved
0.7692	Intermediate Similarity	NPD4693	Phase 3
0.7692	Intermediate Similarity	NPD4138	Approved
0.7692	Intermediate Similarity	NPD5205	Approved
0.7692	Intermediate Similarity	NPD4689	Approved
0.7692	Intermediate Similarity	NPD4690	Approved
0.7692	Intermediate Similarity	NPD4688	Approved
0.7692	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7900	Approved
0.766	Intermediate Similarity	NPD5281	Approved
0.766	Intermediate Similarity	NPD5284	Approved
0.7642	Intermediate Similarity	NPD6868	Approved
0.7634	Intermediate Similarity	NPD6673	Approved
0.7634	Intermediate Similarity	NPD6904	Approved
0.7634	Intermediate Similarity	NPD6080	Approved
0.7624	Intermediate Similarity	NPD4767	Approved
0.7624	Intermediate Similarity	NPD4768	Approved
0.7619	Intermediate Similarity	NPD4632	Approved
0.7604	Intermediate Similarity	NPD5210	Approved
0.7604	Intermediate Similarity	NPD4629	Approved
0.7586	Intermediate Similarity	NPD3617	Approved
0.7586	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7115	Discovery
0.7529	Intermediate Similarity	NPD6926	Approved
0.7529	Intermediate Similarity	NPD6924	Approved
0.7527	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD6001	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.7477	Intermediate Similarity	NPD6274	Approved
0.7476	Intermediate Similarity	NPD5168	Approved
0.7476	Intermediate Similarity	NPD4729	Approved
0.7476	Intermediate Similarity	NPD5128	Approved
0.7476	Intermediate Similarity	NPD4730	Approved
0.7474	Intermediate Similarity	NPD6411	Approved
0.747	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6008	Approved
0.7431	Intermediate Similarity	NPD7100	Approved
0.7431	Intermediate Similarity	NPD7101	Approved
0.7419	Intermediate Similarity	NPD3573	Approved
0.7407	Intermediate Similarity	NPD6317	Approved
0.7407	Intermediate Similarity	NPD6009	Approved
0.7381	Intermediate Similarity	NPD4747	Approved
0.7356	Intermediate Similarity	NPD6933	Approved
0.7339	Intermediate Similarity	NPD6314	Approved
0.7339	Intermediate Similarity	NPD6313	Approved
0.7333	Intermediate Similarity	NPD4692	Approved
0.7333	Intermediate Similarity	NPD5135	Approved
0.7333	Intermediate Similarity	NPD5251	Approved
0.7333	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5249	Phase 3
0.7333	Intermediate Similarity	NPD5250	Approved
0.7333	Intermediate Similarity	NPD5169	Approved
0.7333	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD4139	Approved
0.7333	Intermediate Similarity	NPD5247	Approved
0.7333	Intermediate Similarity	NPD5248	Approved
0.7327	Intermediate Similarity	NPD7632	Discontinued
0.7326	Intermediate Similarity	NPD4784	Approved
0.7326	Intermediate Similarity	NPD4785	Approved
0.7303	Intermediate Similarity	NPD4195	Approved
0.7297	Intermediate Similarity	NPD6909	Approved
0.7297	Intermediate Similarity	NPD6908	Approved
0.7294	Intermediate Similarity	NPD7152	Approved
0.7294	Intermediate Similarity	NPD7150	Approved
0.7294	Intermediate Similarity	NPD7151	Approved
0.7292	Intermediate Similarity	NPD5693	Phase 1
0.7292	Intermediate Similarity	NPD6050	Approved
0.7264	Intermediate Similarity	NPD5215	Approved
0.7264	Intermediate Similarity	NPD5127	Approved
0.7264	Intermediate Similarity	NPD5217	Approved
0.7264	Intermediate Similarity	NPD5216	Approved
0.7263	Intermediate Similarity	NPD6051	Approved
0.7263	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6101	Approved
0.7262	Intermediate Similarity	NPD6923	Approved
0.7262	Intermediate Similarity	NPD4137	Phase 3
0.7262	Intermediate Similarity	NPD6922	Approved
0.7241	Intermediate Similarity	NPD3703	Phase 2
0.7234	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4748	Discontinued
0.7222	Intermediate Similarity	NPD4695	Discontinued
0.7212	Intermediate Similarity	NPD6412	Phase 2
0.7207	Intermediate Similarity	NPD6319	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5692	Phase 3
0.7188	Intermediate Similarity	NPD5207	Approved
0.7176	Intermediate Similarity	NPD7143	Approved
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4244	Approved
0.7176	Intermediate Similarity	NPD4691	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