NPASS Compound

Structure

NPC274724 OpenBabel07101718312D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.5279 -4.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -3.4054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 -2.9189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.9459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 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 1.6852 -1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 2 1 1 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 6 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	4.027
LogD:	2.736
LogS:	-3.453
# Rotatable Bonds:	2
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	2.991
Fsp3:	0.167
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:	-5.003
MDCK Permeability:	7.500984338548733e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.271
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.39677429199219%
Volume Distribution (VD):	0.803
Pgp-substrate:	10.1887845993042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.308
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.723
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.631
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	8.409
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.605
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.669
Skin Sensitization:	0.905
Carcinogencity:	0.059
Eye Corrosion:	0.02
Eye Irritation:	0.929
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC274724

Natural Product ID:	NPC274724
*Common Name:**	11Alpha-Hydroxyurs-12-En-3-One
IUPAC Name:	(4aR,6aR,6bS,8aR,11R,12S,12aR,14R,14aR,14bS)-14-hydroxy-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydropicen-3-one
Synonyms:
Standard InCHIKey:	LRMCLMBQNJUJOA-QIFGSMJJSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-18-9-12-27(5)15-16-29(7)20(24(27)19(18)2)17-21(31)25-28(6)13-11-23(32)26(3,4)22(28)10-14-30(25,29)8/h17-19,21-22,24-25,31H,9-16H2,1-8H3/t18-,19+,21-,22+,24+,25-,27-,28+,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=C[C@H]([C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@H]1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463837
PubChem CID:	21578575
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
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	70400.0	nM	PMID[461051]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	70400.0	nM	PMID[461051]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	70400.0	nM	PMID[461051]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	35200.0	nM	PMID[461051]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	70400.0	nM	PMID[461051]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	35200.0	nM	PMID[461051]

☑ 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 NPC274724 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	193
0.1-0.2	1252
0.2-0.3	4998
0.3-0.4	15040
0.4-0.5	9053
0.5-0.6	5610
0.6-0.7	4713
0.7-0.8	1413
0.8-0.85	284
0.85-0.9	126
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC281524
0.9494	High Similarity	NPC3915
0.9383	High Similarity	NPC180834
0.9375	High Similarity	NPC310989
0.9268	High Similarity	NPC133954
0.9157	High Similarity	NPC475862
0.9157	High Similarity	NPC213412
0.9157	High Similarity	NPC74363
0.9146	High Similarity	NPC227132
0.9048	High Similarity	NPC73064
0.9036	High Similarity	NPC471224
0.8953	High Similarity	NPC198818
0.8929	High Similarity	NPC235341
0.8929	High Similarity	NPC477579
0.8929	High Similarity	NPC95594
0.8929	High Similarity	NPC470955
0.8837	High Similarity	NPC69627
0.8824	High Similarity	NPC307426
0.8824	High Similarity	NPC88716
0.8824	High Similarity	NPC68160
0.8824	High Similarity	NPC130577
0.8824	High Similarity	NPC293564
0.8824	High Similarity	NPC142415
0.8824	High Similarity	NPC173089
0.8824	High Similarity	NPC18064
0.8824	High Similarity	NPC171203
0.8824	High Similarity	NPC242468
0.8824	High Similarity	NPC102683
0.8824	High Similarity	NPC158141
0.8824	High Similarity	NPC51700
0.8824	High Similarity	NPC98442
0.881	High Similarity	NPC474083
0.878	High Similarity	NPC274050
0.878	High Similarity	NPC263272
0.878	High Similarity	NPC162632
0.878	High Similarity	NPC267691
0.875	High Similarity	NPC74995
0.875	High Similarity	NPC169343
0.8736	High Similarity	NPC291028
0.8736	High Similarity	NPC193750
0.8736	High Similarity	NPC46441
0.8721	High Similarity	NPC52169
0.8721	High Similarity	NPC470629
0.8721	High Similarity	NPC40552
0.8721	High Similarity	NPC246708
0.8721	High Similarity	NPC290690
0.8721	High Similarity	NPC1753
0.8721	High Similarity	NPC182797
0.8721	High Similarity	NPC17733
0.8721	High Similarity	NPC474511
0.8721	High Similarity	NPC181225
0.8721	High Similarity	NPC473242
0.8721	High Similarity	NPC474512
0.8706	High Similarity	NPC322159
0.8706	High Similarity	NPC469994
0.8706	High Similarity	NPC72638
0.869	High Similarity	NPC476412
0.8675	High Similarity	NPC69101
0.8675	High Similarity	NPC251779
0.8675	High Similarity	NPC163236
0.8659	High Similarity	NPC2482
0.8659	High Similarity	NPC295131
0.8652	High Similarity	NPC91010
0.8652	High Similarity	NPC87095
0.8652	High Similarity	NPC474882
0.8642	High Similarity	NPC297996
0.8636	High Similarity	NPC4036
0.8636	High Similarity	NPC6255
0.8636	High Similarity	NPC233455
0.8636	High Similarity	NPC145067
0.8636	High Similarity	NPC471588
0.8636	High Similarity	NPC105189
0.8636	High Similarity	NPC38754
0.8636	High Similarity	NPC65120
0.8636	High Similarity	NPC474525
0.8636	High Similarity	NPC158030
0.8621	High Similarity	NPC130520
0.8621	High Similarity	NPC127689
0.8621	High Similarity	NPC121798
0.8621	High Similarity	NPC263393
0.8621	High Similarity	NPC225585
0.8621	High Similarity	NPC290972
0.8621	High Similarity	NPC473999
0.8621	High Similarity	NPC161751
0.8621	High Similarity	NPC309603
0.8621	High Similarity	NPC470588
0.8621	High Similarity	NPC274330
0.8621	High Similarity	NPC474972
0.8621	High Similarity	NPC270768
0.8621	High Similarity	NPC293048
0.8621	High Similarity	NPC59263
0.8621	High Similarity	NPC143232
0.8621	High Similarity	NPC234346
0.8621	High Similarity	NPC2983
0.8621	High Similarity	NPC25906
0.8621	High Similarity	NPC198664
0.8621	High Similarity	NPC95246
0.8621	High Similarity	NPC61543
0.8621	High Similarity	NPC64872
0.8605	High Similarity	NPC71507
0.8588	High Similarity	NPC476426
0.8571	High Similarity	NPC70834
0.8556	High Similarity	NPC290481
0.8554	High Similarity	NPC474484
0.8554	High Similarity	NPC103754
0.8539	High Similarity	NPC295643
0.8539	High Similarity	NPC272075
0.8539	High Similarity	NPC118490
0.8539	High Similarity	NPC214756
0.8537	High Similarity	NPC152061
0.8537	High Similarity	NPC16394
0.8537	High Similarity	NPC308038
0.8523	High Similarity	NPC48010
0.8523	High Similarity	NPC210037
0.8523	High Similarity	NPC18872
0.8523	High Similarity	NPC227467
0.8523	High Similarity	NPC470589
0.8523	High Similarity	NPC290614
0.8523	High Similarity	NPC477872
0.8523	High Similarity	NPC126369
0.8523	High Similarity	NPC86372
0.8523	High Similarity	NPC130278
0.8523	High Similarity	NPC120968
0.8523	High Similarity	NPC7260
0.8523	High Similarity	NPC111110
0.8523	High Similarity	NPC273621
0.8523	High Similarity	NPC172361
0.8506	High Similarity	NPC474474
0.8506	High Similarity	NPC472802
0.8488	Intermediate Similarity	NPC472985
0.8488	Intermediate Similarity	NPC82979
0.8488	Intermediate Similarity	NPC472986
0.8488	Intermediate Similarity	NPC158393
0.8471	Intermediate Similarity	NPC221758
0.8471	Intermediate Similarity	NPC214043
0.8471	Intermediate Similarity	NPC473157
0.8471	Intermediate Similarity	NPC82902
0.8471	Intermediate Similarity	NPC85774
0.8471	Intermediate Similarity	NPC96095
0.8471	Intermediate Similarity	NPC59453
0.8462	Intermediate Similarity	NPC116457
0.8452	Intermediate Similarity	NPC48362
0.8452	Intermediate Similarity	NPC212083
0.8452	Intermediate Similarity	NPC151519
0.8444	Intermediate Similarity	NPC474529
0.8434	Intermediate Similarity	NPC306095
0.8434	Intermediate Similarity	NPC104120
0.8434	Intermediate Similarity	NPC157895
0.8434	Intermediate Similarity	NPC148685
0.8434	Intermediate Similarity	NPC267517
0.8427	Intermediate Similarity	NPC966
0.8427	Intermediate Similarity	NPC324341
0.8427	Intermediate Similarity	NPC282616
0.8427	Intermediate Similarity	NPC288833
0.8427	Intermediate Similarity	NPC475806
0.8427	Intermediate Similarity	NPC84319
0.8427	Intermediate Similarity	NPC52021
0.8427	Intermediate Similarity	NPC71074
0.8427	Intermediate Similarity	NPC300351
0.8427	Intermediate Similarity	NPC306541
0.8427	Intermediate Similarity	NPC187722
0.8427	Intermediate Similarity	NPC25299
0.8427	Intermediate Similarity	NPC235884
0.8427	Intermediate Similarity	NPC228784
0.8427	Intermediate Similarity	NPC472149
0.8427	Intermediate Similarity	NPC473998
0.8427	Intermediate Similarity	NPC155120
0.8415	Intermediate Similarity	NPC239098
0.8409	Intermediate Similarity	NPC474700
0.8409	Intermediate Similarity	NPC472973
0.8409	Intermediate Similarity	NPC474686
0.8395	Intermediate Similarity	NPC263582
0.8391	Intermediate Similarity	NPC93778
0.8391	Intermediate Similarity	NPC317590
0.8372	Intermediate Similarity	NPC474218
0.8372	Intermediate Similarity	NPC292553
0.837	Intermediate Similarity	NPC189880
0.8353	Intermediate Similarity	NPC307258
0.8353	Intermediate Similarity	NPC200752
0.8353	Intermediate Similarity	NPC53733
0.8353	Intermediate Similarity	NPC215893
0.8353	Intermediate Similarity	NPC105173
0.8352	Intermediate Similarity	NPC148523
0.8352	Intermediate Similarity	NPC139570
0.8333	Intermediate Similarity	NPC298554
0.8333	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC86368
0.8333	Intermediate Similarity	NPC275809
0.8333	Intermediate Similarity	NPC158059
0.8333	Intermediate Similarity	NPC307335
0.8333	Intermediate Similarity	NPC121984
0.8333	Intermediate Similarity	NPC474436
0.8333	Intermediate Similarity	NPC136313
0.8333	Intermediate Similarity	NPC49776
0.8333	Intermediate Similarity	NPC63118
0.8333	Intermediate Similarity	NPC74855
0.8333	Intermediate Similarity	NPC471898
0.8333	Intermediate Similarity	NPC202728
0.8333	Intermediate Similarity	NPC14151
0.8333	Intermediate Similarity	NPC141447

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 NPC274724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1596
0.2-0.3	3931
0.3-0.4	2381
0.4-0.5	633
0.5-0.6	188
0.6-0.7	205
0.7-0.8	36
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD7515	Phase 2
0.8471	Intermediate Similarity	NPD4786	Approved
0.8452	Intermediate Similarity	NPD3667	Approved
0.8256	Intermediate Similarity	NPD3666	Approved
0.8256	Intermediate Similarity	NPD3133	Approved
0.8256	Intermediate Similarity	NPD3665	Phase 1
0.8242	Intermediate Similarity	NPD7748	Approved
0.8095	Intermediate Similarity	NPD7645	Phase 2
0.8068	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD5328	Approved
0.7979	Intermediate Similarity	NPD7902	Approved
0.7865	Intermediate Similarity	NPD4623	Approved
0.7865	Intermediate Similarity	NPD4519	Discontinued
0.7826	Intermediate Similarity	NPD6079	Approved
0.7753	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.766	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7900	Approved
0.764	Intermediate Similarity	NPD3668	Phase 3
0.7614	Intermediate Similarity	NPD4221	Approved
0.7614	Intermediate Similarity	NPD4223	Phase 3
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7609	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4695	Discontinued
0.7556	Intermediate Similarity	NPD5329	Approved
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.7553	Intermediate Similarity	NPD4202	Approved
0.7528	Intermediate Similarity	NPD4788	Approved
0.7473	Intermediate Similarity	NPD7146	Approved
0.7473	Intermediate Similarity	NPD6684	Approved
0.7473	Intermediate Similarity	NPD7521	Approved
0.7473	Intermediate Similarity	NPD7334	Approved
0.7473	Intermediate Similarity	NPD6409	Approved
0.7473	Intermediate Similarity	NPD5330	Approved
0.7444	Intermediate Similarity	NPD4197	Approved
0.7412	Intermediate Similarity	NPD7339	Approved
0.7412	Intermediate Similarity	NPD6942	Approved
0.7356	Intermediate Similarity	NPD3617	Approved
0.7326	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6903	Approved
0.73	Intermediate Similarity	NPD5211	Phase 2
0.7283	Intermediate Similarity	NPD4138	Approved
0.7283	Intermediate Similarity	NPD4689	Approved
0.7283	Intermediate Similarity	NPD4690	Approved
0.7283	Intermediate Similarity	NPD4688	Approved
0.7283	Intermediate Similarity	NPD4693	Phase 3
0.7283	Intermediate Similarity	NPD5205	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD6084	Phase 2
0.7245	Intermediate Similarity	NPD6083	Phase 2
0.7245	Intermediate Similarity	NPD4755	Approved
0.7216	Intermediate Similarity	NPD4629	Approved
0.7216	Intermediate Similarity	NPD5210	Approved
0.7191	Intermediate Similarity	NPD7525	Registered
0.7172	Intermediate Similarity	NPD7638	Approved
0.7159	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD7614	Phase 1
0.7143	Intermediate Similarity	NPD4244	Approved
0.7143	Intermediate Similarity	NPD4245	Approved
0.7128	Intermediate Similarity	NPD5737	Approved
0.7128	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD4700	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.7097	Intermediate Similarity	NPD4694	Approved
0.7097	Intermediate Similarity	NPD5280	Approved
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8034	Phase 2
0.7083	Intermediate Similarity	NPD8035	Phase 2
0.7059	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5223	Approved
0.7024	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4137	Phase 3
0.7024	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3698	Phase 2
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6412	Phase 2
0.7011	Intermediate Similarity	NPD8264	Approved
0.6961	Remote Similarity	NPD5224	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5225	Approved
0.6941	Remote Similarity	NPD4747	Approved
0.6941	Remote Similarity	NPD4789	Approved
0.6941	Remote Similarity	NPD4691	Approved
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6915	Remote Similarity	NPD6098	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD6411	Approved
0.6905	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6926	Approved
0.6897	Remote Similarity	NPD6924	Approved
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6889	Remote Similarity	NPD4195	Approved
0.6889	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD4243	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3573	Approved
0.6837	Remote Similarity	NPD5779	Approved
0.6837	Remote Similarity	NPD5778	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6813	Remote Similarity	NPD6930	Phase 2
0.6813	Remote Similarity	NPD6931	Approved
0.68	Remote Similarity	NPD7732	Phase 3
0.6792	Remote Similarity	NPD6881	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD7320	Approved
0.6778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4767	Approved
0.6762	Remote Similarity	NPD4768	Approved
0.6747	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6933	Approved
0.6739	Remote Similarity	NPD8028	Phase 2
0.6735	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD5284	Approved
0.6729	Remote Similarity	NPD6373	Approved
0.6729	Remote Similarity	NPD6372	Approved
0.6705	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4058	Approved
0.6705	Remote Similarity	NPD4784	Approved
0.6705	Remote Similarity	NPD4785	Approved
0.6705	Remote Similarity	NPD5733	Approved
0.6701	Remote Similarity	NPD6080	Approved
0.6701	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD6101	Approved
0.6701	Remote Similarity	NPD6673	Approved
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5701	Approved
0.6698	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4269	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6635	Remote Similarity	NPD7632	Discontinued
0.6633	Remote Similarity	NPD4096	Approved
0.6632	Remote Similarity	NPD1694	Approved
0.6632	Remote Similarity	NPD1696	Phase 3
0.663	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD7514	Phase 3
0.6629	Remote Similarity	NPD3703	Phase 2
0.6628	Remote Similarity	NPD6922	Approved
0.6628	Remote Similarity	NPD6923	Approved
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6649	Approved
0.6602	Remote Similarity	NPD6404	Discontinued
0.6598	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD6695	Phase 3
0.6593	Remote Similarity	NPD7145	Approved
0.6585	Remote Similarity	NPD368	Approved
0.6574	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD6014	Approved
0.6574	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6013	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD5693	Phase 1
0.6559	Remote Similarity	NPD6902	Approved
0.6556	Remote Similarity	NPD6117	Approved
0.6552	Remote Similarity	NPD8328	Phase 3
0.6552	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD7144	Approved
0.6548	Remote Similarity	NPD7341	Phase 2
0.6545	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD6356	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