NPASS Compound

Structure

NPC310989 OpenBabel07101718232D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.7797 0.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2998 2.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1861 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 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 -0.8426 -1.4595 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 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 -1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 2.4324 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 4.2131 -1.4595 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 1.6852 -1.9459 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 4.6996 0.3561 0.0000 C 0 0 0 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 2.5279 -0.4865 0.0000 C 0 0 0 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 -0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 0 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 4.2131 -0.4865 0.0000 C 0 0 1 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 -0.8426 1.4595 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 5.6726 0.3561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 2.9189 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 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 32 2 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	5.424
LogD:	4.636
LogS:	-5.506
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	4.888
Fsp3:	0.9
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:	-5.239
MDCK Permeability:	9.824167136684991e-06
Pgp-inhibitor:	0.063
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.35
Plasma Protein Binding (PPB):	92.56786346435547%
Volume Distribution (VD):	1.045
Pgp-substrate:	1.8215848207473755%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.154
CYP2C9-substrate:	0.332
CYP2D6-inhibitor:	0.115
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.81

ADMET: Excretion

Clearance (CL):	5.473
Half-life (T1/2):	0.329

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.077
Carcinogencity:	0.041
Eye Corrosion:	0.06
Eye Irritation:	0.144
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: NPC310989

Natural Product ID:	NPC310989
*Common Name:**	29-Hydroxy-3-Oxo-Olean-18-Ene
IUPAC Name:	(4aR,6aS,6aR,6bR,8aS,11R,14aR,14bR)-11-(hydroxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-2,4a,5,6,6a,7,8,9,10,13,14,14a-dodecahydro-1H-picen-3-one
Synonyms:
Standard InCHIKey:	YMNLXMXTZKUAJB-RLLULNRHSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-25(2)22-10-13-30(7)23(28(22,5)12-11-24(25)32)9-8-20-21-18-26(3,19-31)14-15-27(21,4)16-17-29(20,30)6/h18,20,22-23,31H,8-17,19H2,1-7H3/t20-,22+,23-,26-,27-,28+,29-,30-/m1/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4C5=C[C@@](C)(CC[C@]5(C)CC[C@@]34C)CO)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022919
PubChem CID:	60145668
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
NPO33201	celastraceae sp.	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22487595]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	50.0	%	PMID[465014]

☑ 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 NPC310989 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	190
0.1-0.2	1282
0.2-0.3	5524
0.3-0.4	16299
0.4-0.5	7908
0.5-0.6	5406
0.6-0.7	4311
0.7-0.8	1320
0.8-0.85	267
0.85-0.9	152
0.9-0.95	35
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC3915
0.9744	High Similarity	NPC180834
0.9383	High Similarity	NPC73064
0.9375	High Similarity	NPC133954
0.9375	High Similarity	NPC274724
0.9268	High Similarity	NPC474511
0.9268	High Similarity	NPC1753
0.9259	High Similarity	NPC74363
0.9259	High Similarity	NPC475862
0.9259	High Similarity	NPC213412
0.9241	High Similarity	NPC251779
0.9241	High Similarity	NPC69101
0.9231	High Similarity	NPC2482
0.9146	High Similarity	NPC158141
0.9146	High Similarity	NPC173089
0.9114	High Similarity	NPC263272
0.9114	High Similarity	NPC267691
0.9114	High Similarity	NPC274050
0.9114	High Similarity	NPC162632
0.9036	High Similarity	NPC474474
0.9036	High Similarity	NPC17733
0.9036	High Similarity	NPC474512
0.9036	High Similarity	NPC470629
0.9036	High Similarity	NPC290690
0.9036	High Similarity	NPC181225
0.9036	High Similarity	NPC473242
0.9024	High Similarity	NPC477579
0.9024	High Similarity	NPC95594
0.9024	High Similarity	NPC235341
0.8941	High Similarity	NPC38754
0.8929	High Similarity	NPC470588
0.8929	High Similarity	NPC274330
0.8929	High Similarity	NPC474700
0.8929	High Similarity	NPC69627
0.8929	High Similarity	NPC281524
0.8929	High Similarity	NPC198664
0.8929	High Similarity	NPC143232
0.8916	High Similarity	NPC142415
0.8916	High Similarity	NPC171203
0.8916	High Similarity	NPC71507
0.8916	High Similarity	NPC18064
0.8916	High Similarity	NPC242468
0.8916	High Similarity	NPC98442
0.8916	High Similarity	NPC88716
0.8916	High Similarity	NPC51700
0.8916	High Similarity	NPC307426
0.8916	High Similarity	NPC130577
0.8916	High Similarity	NPC68160
0.8916	High Similarity	NPC293564
0.8916	High Similarity	NPC102683
0.8889	High Similarity	NPC70834
0.8875	High Similarity	NPC121984
0.8861	High Similarity	NPC16394
0.8824	High Similarity	NPC111110
0.8824	High Similarity	NPC46441
0.8824	High Similarity	NPC126369
0.8824	High Similarity	NPC193750
0.8824	High Similarity	NPC291028
0.8824	High Similarity	NPC470589
0.881	High Similarity	NPC52169
0.881	High Similarity	NPC40552
0.881	High Similarity	NPC182797
0.881	High Similarity	NPC246708
0.8795	High Similarity	NPC72638
0.878	High Similarity	NPC312660
0.878	High Similarity	NPC59453
0.878	High Similarity	NPC96095
0.878	High Similarity	NPC221758
0.8765	High Similarity	NPC163236
0.8765	High Similarity	NPC212083
0.8765	High Similarity	NPC151519
0.875	High Similarity	NPC267517
0.8736	High Similarity	NPC148964
0.8721	High Similarity	NPC145067
0.8721	High Similarity	NPC471588
0.8721	High Similarity	NPC187722
0.8721	High Similarity	NPC105189
0.8721	High Similarity	NPC6255
0.8721	High Similarity	NPC474525
0.8721	High Similarity	NPC233455
0.8721	High Similarity	NPC158030
0.8721	High Similarity	NPC4036
0.8721	High Similarity	NPC65120
0.8706	High Similarity	NPC121798
0.8706	High Similarity	NPC161751
0.8706	High Similarity	NPC263393
0.8706	High Similarity	NPC64872
0.8706	High Similarity	NPC474686
0.8706	High Similarity	NPC61543
0.8706	High Similarity	NPC477973
0.8706	High Similarity	NPC293048
0.8706	High Similarity	NPC290972
0.8706	High Similarity	NPC225585
0.8706	High Similarity	NPC234346
0.8706	High Similarity	NPC127689
0.8706	High Similarity	NPC270768
0.8706	High Similarity	NPC25906
0.8706	High Similarity	NPC95246
0.8706	High Similarity	NPC59263
0.8706	High Similarity	NPC130520
0.8706	High Similarity	NPC474972
0.869	High Similarity	NPC93778
0.8675	High Similarity	NPC469948
0.8675	High Similarity	NPC469993
0.8659	High Similarity	NPC307258
0.8659	High Similarity	NPC200752
0.8659	High Similarity	NPC53733
0.8642	High Similarity	NPC471898
0.8642	High Similarity	NPC14151
0.8625	High Similarity	NPC199595
0.8625	High Similarity	NPC201459
0.8625	High Similarity	NPC474113
0.8625	High Similarity	NPC231431
0.8621	High Similarity	NPC214756
0.8621	High Similarity	NPC272075
0.8621	High Similarity	NPC118519
0.8621	High Similarity	NPC202728
0.8621	High Similarity	NPC158059
0.8621	High Similarity	NPC229281
0.8621	High Similarity	NPC295643
0.8621	High Similarity	NPC118490
0.8608	High Similarity	NPC471899
0.8608	High Similarity	NPC107039
0.8608	High Similarity	NPC471897
0.8605	High Similarity	NPC130278
0.8605	High Similarity	NPC198818
0.8605	High Similarity	NPC273621
0.8605	High Similarity	NPC210037
0.8605	High Similarity	NPC477872
0.8605	High Similarity	NPC86372
0.8605	High Similarity	NPC120968
0.8605	High Similarity	NPC290614
0.8605	High Similarity	NPC474728
0.8605	High Similarity	NPC7260
0.8605	High Similarity	NPC172361
0.8605	High Similarity	NPC227467
0.8605	High Similarity	NPC18872
0.8588	High Similarity	NPC230387
0.8588	High Similarity	NPC206060
0.8588	High Similarity	NPC472802
0.8571	High Similarity	NPC474732
0.8571	High Similarity	NPC145879
0.8571	High Similarity	NPC158393
0.8571	High Similarity	NPC56588
0.8571	High Similarity	NPC31564
0.8571	High Similarity	NPC51014
0.8571	High Similarity	NPC474733
0.8571	High Similarity	NPC474778
0.8571	High Similarity	NPC324063
0.8571	High Similarity	NPC470955
0.8554	High Similarity	NPC214043
0.8554	High Similarity	NPC82902
0.8554	High Similarity	NPC227132
0.8554	High Similarity	NPC85774
0.8539	High Similarity	NPC157113
0.8539	High Similarity	NPC62516
0.8537	High Similarity	NPC48362
0.8523	High Similarity	NPC209868
0.8523	High Similarity	NPC87095
0.8523	High Similarity	NPC159365
0.8523	High Similarity	NPC6818
0.8523	High Similarity	NPC474529
0.8523	High Similarity	NPC191412
0.8523	High Similarity	NPC23170
0.8523	High Similarity	NPC114159
0.8519	High Similarity	NPC37038
0.8519	High Similarity	NPC472478
0.8519	High Similarity	NPC18955
0.8519	High Similarity	NPC104545
0.8506	High Similarity	NPC228784
0.8506	High Similarity	NPC288833
0.8506	High Similarity	NPC470590
0.8506	High Similarity	NPC301244
0.8506	High Similarity	NPC52021
0.8506	High Similarity	NPC324341
0.8506	High Similarity	NPC966
0.8506	High Similarity	NPC282616
0.8506	High Similarity	NPC300351
0.8506	High Similarity	NPC77099
0.8506	High Similarity	NPC71074
0.8506	High Similarity	NPC84319
0.8506	High Similarity	NPC472149
0.8506	High Similarity	NPC235884
0.8506	High Similarity	NPC25299
0.8506	High Similarity	NPC155120
0.8506	High Similarity	NPC285184
0.8506	High Similarity	NPC306541
0.8506	High Similarity	NPC60755
0.85	High Similarity	NPC474989
0.85	High Similarity	NPC99168
0.85	High Similarity	NPC22955
0.85	High Similarity	NPC470396
0.85	High Similarity	NPC260385
0.85	High Similarity	NPC110094
0.85	High Similarity	NPC280654
0.8488	Intermediate Similarity	NPC184663
0.8481	Intermediate Similarity	NPC106364
0.8481	Intermediate Similarity	NPC89294
0.8471	Intermediate Similarity	NPC58063
0.8471	Intermediate Similarity	NPC475740

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 NPC310989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1660
0.2-0.3	4005
0.3-0.4	2311
0.4-0.5	576
0.5-0.6	184
0.6-0.7	184
0.7-0.8	52
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD4786	Approved
0.8765	High Similarity	NPD3667	Approved
0.8721	High Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD3666	Approved
0.8333	Intermediate Similarity	NPD3665	Phase 1
0.8333	Intermediate Similarity	NPD3133	Approved
0.8315	Intermediate Similarity	NPD7748	Approved
0.8171	Intermediate Similarity	NPD7645	Phase 2
0.814	Intermediate Similarity	NPD3618	Phase 1
0.8072	Intermediate Similarity	NPD4695	Discontinued
0.8068	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD5328	Approved
0.8043	Intermediate Similarity	NPD7902	Approved
0.7907	Intermediate Similarity	NPD3668	Phase 3
0.7889	Intermediate Similarity	NPD6079	Approved
0.7882	Intermediate Similarity	NPD4223	Phase 3
0.7882	Intermediate Similarity	NPD4221	Approved
0.7865	Intermediate Similarity	NPD4753	Phase 2
0.7816	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5329	Approved
0.7802	Intermediate Similarity	NPD6399	Phase 3
0.7791	Intermediate Similarity	NPD4788	Approved
0.7753	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5279	Phase 3
0.7717	Intermediate Similarity	NPD7900	Approved
0.7717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4197	Approved
0.7683	Intermediate Similarity	NPD6942	Approved
0.7683	Intermediate Similarity	NPD7339	Approved
0.7619	Intermediate Similarity	NPD3617	Approved
0.7609	Intermediate Similarity	NPD4202	Approved
0.759	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4623	Approved
0.7528	Intermediate Similarity	NPD4519	Discontinued
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD5205	Approved
0.7528	Intermediate Similarity	NPD4689	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.7528	Intermediate Similarity	NPD4688	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.7528	Intermediate Similarity	NPD4690	Approved
0.7528	Intermediate Similarity	NPD4693	Phase 3
0.7528	Intermediate Similarity	NPD4138	Approved
0.7474	Intermediate Similarity	NPD6084	Phase 2
0.7474	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD4629	Approved
0.7447	Intermediate Similarity	NPD5210	Approved
0.7368	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD7614	Phase 1
0.7368	Intermediate Similarity	NPD5222	Approved
0.7363	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD5737	Approved
0.7333	Intermediate Similarity	NPD5690	Phase 2
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4694	Approved
0.7333	Intermediate Similarity	NPD5280	Approved
0.7292	Intermediate Similarity	NPD4755	Approved
0.7292	Intermediate Similarity	NPD5173	Approved
0.7284	Intermediate Similarity	NPD4137	Phase 3
0.7241	Intermediate Similarity	NPD7525	Registered
0.7195	Intermediate Similarity	NPD4245	Approved
0.7195	Intermediate Similarity	NPD4747	Approved
0.7195	Intermediate Similarity	NPD4789	Approved
0.7195	Intermediate Similarity	NPD4691	Approved
0.7195	Intermediate Similarity	NPD4244	Approved
0.716	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4692	Approved
0.7159	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD6926	Approved
0.7143	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD4785	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD6411	Approved
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7126	Intermediate Similarity	NPD4195	Approved
0.7108	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4243	Approved
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7073	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3698	Phase 2
0.7071	Intermediate Similarity	NPD5223	Approved
0.7065	Intermediate Similarity	NPD3573	Approved
0.7059	Intermediate Similarity	NPD6412	Phase 2
0.7041	Intermediate Similarity	NPD5696	Approved
0.701	Intermediate Similarity	NPD7732	Phase 3
0.7	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD5224	Approved
0.6977	Remote Similarity	NPD6933	Approved
0.6966	Remote Similarity	NPD8028	Phase 2
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6941	Remote Similarity	NPD5733	Approved
0.6941	Remote Similarity	NPD4058	Approved
0.6931	Remote Similarity	NPD4754	Approved
0.6931	Remote Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD5174	Approved
0.6915	Remote Similarity	NPD6080	Approved
0.6915	Remote Similarity	NPD6101	Approved
0.6915	Remote Similarity	NPD6673	Approved
0.6915	Remote Similarity	NPD6904	Approved
0.6915	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7331	Phase 2
0.6869	Remote Similarity	NPD7638	Approved
0.6867	Remote Similarity	NPD6923	Approved
0.6867	Remote Similarity	NPD6922	Approved
0.6863	Remote Similarity	NPD5141	Approved
0.6854	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4096	Approved
0.6827	Remote Similarity	NPD7320	Approved
0.6827	Remote Similarity	NPD6899	Approved
0.6827	Remote Similarity	NPD6881	Approved
0.6809	Remote Similarity	NPD5208	Approved
0.6809	Remote Similarity	NPD4518	Approved
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD4767	Approved
0.679	Remote Similarity	NPD7341	Phase 2
0.6786	Remote Similarity	NPD7143	Approved
0.6786	Remote Similarity	NPD7144	Approved
0.6762	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD6372	Approved
0.6747	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5360	Phase 3
0.6744	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4687	Approved
0.6742	Remote Similarity	NPD6929	Approved
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5701	Approved
0.6731	Remote Similarity	NPD5697	Approved
0.6707	Remote Similarity	NPD4224	Phase 2
0.6706	Remote Similarity	NPD7150	Approved
0.6706	Remote Similarity	NPD5276	Approved
0.6706	Remote Similarity	NPD7152	Approved
0.6706	Remote Similarity	NPD7151	Approved
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5133	Approved
0.6698	Remote Similarity	NPD6883	Approved
0.6698	Remote Similarity	NPD7290	Approved
0.6698	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD5275	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6636	Remote Similarity	NPD6869	Approved
0.6629	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD6014	Approved
0.6604	Remote Similarity	NPD6013	Approved
0.6598	Remote Similarity	NPD6050	Approved
0.6598	Remote Similarity	NPD5693	Phase 1
0.6591	Remote Similarity	NPD6117	Approved
0.6579	Remote Similarity	NPD8328	Phase 3
0.6574	Remote Similarity	NPD8297	Approved
0.6574	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD5250	Approved
0.6542	Remote Similarity	NPD5251	Approved
0.6542	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5247	Approved
0.6542	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD5135	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