NPASS Compound

Structure

CID162632 OpenBabel06191715532D 33 37 0 0 1 0 0 0 0 0999 V2000 2.5297 4.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 -2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0429 -2.3038 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 0.8432 -0.4868 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 3.3729 2.9211 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 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 -0.0000 -0.9737 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 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 2.5297 3.4079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 2.9211 0.0000 C 0 0 1 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 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3729 0.9737 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 -1.6865 0.0000 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 3 0 0 0 0 0 0 0 0 0 -4.2162 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 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 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 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 28 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 2 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 25 32 2 0 0 0 0 25 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	6.184
LogD:	5.33
LogS:	-5.269
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.701
Fsp3:	0.867
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:	-5.394
MDCK Permeability:	1.1612307389441412e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	98.21617889404297%
Volume Distribution (VD):	0.74
Pgp-substrate:	2.1382434368133545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.743
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.194
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	2.667
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.483
Skin Sensitization:	0.025
Carcinogencity:	0.089
Eye Corrosion:	0.032
Eye Irritation:	0.463
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: NPC162632

Natural Product ID:	NPC162632
*Common Name:**	1,2,6A,6B,9,9,12A-Heptamethyl-10-Oxo-1,3,4,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-Octadecahydro-2H-Picene-4A-Carboxylic Acid
IUPAC Name:	(1S,2R,6aR,6aS,6bR,8aR,12aR)-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	MUCRYNWJQNHDJH-VTVIAGDMSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-22,24H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,24?,27+,28-,29-,30?/m1/s1
SMILES:	C[C@@H]1CCC2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)C2[C@H]1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL417927
PubChem CID:	10939393
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
NPO11518.1	Strophanthus sarmentosus var. senegambiae	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24213	Strophanthus thollonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24213	Strophanthus thollonii	Species	Apocynaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	22.0	%	PMID[453886]

☑ 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 NPC162632 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	189
0.1-0.2	1350
0.2-0.3	6467
0.3-0.4	16179
0.4-0.5	7501
0.5-0.6	5470
0.6-0.7	4016
0.7-0.8	1100
0.8-0.85	202
0.85-0.9	172
0.9-0.95	40
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274050
1.0	High Similarity	NPC267691
1.0	High Similarity	NPC263272
0.9868	High Similarity	NPC69101
0.9868	High Similarity	NPC251779
0.974	High Similarity	NPC70834
0.9733	High Similarity	NPC16394
0.9615	High Similarity	NPC96095
0.9481	High Similarity	NPC471898
0.9474	High Similarity	NPC231431
0.9467	High Similarity	NPC471899
0.9467	High Similarity	NPC471897
0.9467	High Similarity	NPC107039
0.9351	High Similarity	NPC37038
0.9351	High Similarity	NPC267517
0.9342	High Similarity	NPC110094
0.9342	High Similarity	NPC260385
0.9342	High Similarity	NPC280654
0.9333	High Similarity	NPC89294
0.9259	High Similarity	NPC158141
0.9259	High Similarity	NPC173089
0.925	High Similarity	NPC474537
0.9241	High Similarity	NPC200752
0.9231	High Similarity	NPC142244
0.9231	High Similarity	NPC3915
0.9221	High Similarity	NPC199595
0.9146	High Similarity	NPC1753
0.9146	High Similarity	NPC474474
0.9146	High Similarity	NPC474511
0.9114	High Similarity	NPC310989
0.9103	High Similarity	NPC104545
0.9036	High Similarity	NPC281524
0.9036	High Similarity	NPC474700
0.9024	High Similarity	NPC142415
0.9024	High Similarity	NPC18064
0.9024	High Similarity	NPC242468
0.9024	High Similarity	NPC171203
0.9024	High Similarity	NPC98442
0.9024	High Similarity	NPC51700
0.9024	High Similarity	NPC307426
0.9024	High Similarity	NPC130577
0.9024	High Similarity	NPC102683
0.9024	High Similarity	NPC68160
0.9024	High Similarity	NPC88716
0.9024	High Similarity	NPC293564
0.8987	High Similarity	NPC278459
0.8987	High Similarity	NPC221647
0.8987	High Similarity	NPC147066
0.8961	High Similarity	NPC165711
0.8947	High Similarity	NPC192540
0.8947	High Similarity	NPC279666
0.8933	High Similarity	NPC36310
0.8929	High Similarity	NPC46441
0.8929	High Similarity	NPC193750
0.8929	High Similarity	NPC291028
0.8929	High Similarity	NPC198818
0.8916	High Similarity	NPC290690
0.8916	High Similarity	NPC473242
0.8916	High Similarity	NPC246708
0.8916	High Similarity	NPC470629
0.8916	High Similarity	NPC182797
0.8916	High Similarity	NPC17733
0.8916	High Similarity	NPC40552
0.8916	High Similarity	NPC474512
0.8916	High Similarity	NPC181225
0.8916	High Similarity	NPC52169
0.8902	High Similarity	NPC72638
0.8889	High Similarity	NPC156981
0.8889	High Similarity	NPC312660
0.8889	High Similarity	NPC180834
0.8861	High Similarity	NPC477057
0.8831	High Similarity	NPC69143
0.8824	High Similarity	NPC4036
0.8824	High Similarity	NPC474525
0.8824	High Similarity	NPC233455
0.8824	High Similarity	NPC145067
0.8824	High Similarity	NPC65120
0.8824	High Similarity	NPC158030
0.8824	High Similarity	NPC471588
0.8824	High Similarity	NPC105189
0.8824	High Similarity	NPC38754
0.8824	High Similarity	NPC6255
0.8816	High Similarity	NPC283908
0.8816	High Similarity	NPC251970
0.8816	High Similarity	NPC183503
0.8816	High Similarity	NPC161923
0.8816	High Similarity	NPC255168
0.8816	High Similarity	NPC476046
0.8816	High Similarity	NPC241854
0.8816	High Similarity	NPC103958
0.881	High Similarity	NPC274330
0.881	High Similarity	NPC95246
0.881	High Similarity	NPC234346
0.881	High Similarity	NPC293048
0.881	High Similarity	NPC270768
0.881	High Similarity	NPC290972
0.881	High Similarity	NPC61543
0.881	High Similarity	NPC161751
0.881	High Similarity	NPC263393
0.881	High Similarity	NPC130520
0.881	High Similarity	NPC470588
0.881	High Similarity	NPC25906
0.881	High Similarity	NPC59263
0.881	High Similarity	NPC225585
0.881	High Similarity	NPC127689
0.881	High Similarity	NPC143232
0.881	High Similarity	NPC64872
0.881	High Similarity	NPC198664
0.881	High Similarity	NPC121798
0.881	High Similarity	NPC474972
0.88	High Similarity	NPC160817
0.8795	High Similarity	NPC71507
0.878	High Similarity	NPC133954
0.878	High Similarity	NPC274724
0.8765	High Similarity	NPC53733
0.875	High Similarity	NPC201912
0.875	High Similarity	NPC38350
0.8734	High Similarity	NPC192744
0.8734	High Similarity	NPC477371
0.8721	High Similarity	NPC272075
0.8721	High Similarity	NPC214756
0.8721	High Similarity	NPC169343
0.8721	High Similarity	NPC118490
0.8721	High Similarity	NPC295643
0.8706	High Similarity	NPC227467
0.8706	High Similarity	NPC290614
0.8706	High Similarity	NPC126369
0.8706	High Similarity	NPC130278
0.8706	High Similarity	NPC86372
0.8706	High Similarity	NPC120968
0.8706	High Similarity	NPC210037
0.8706	High Similarity	NPC474728
0.8706	High Similarity	NPC113989
0.8706	High Similarity	NPC273621
0.8706	High Similarity	NPC120840
0.8706	High Similarity	NPC172361
0.8706	High Similarity	NPC18872
0.8706	High Similarity	NPC470589
0.8706	High Similarity	NPC477872
0.8706	High Similarity	NPC111110
0.8706	High Similarity	NPC7260
0.8675	High Similarity	NPC74363
0.8675	High Similarity	NPC324063
0.8675	High Similarity	NPC475862
0.8675	High Similarity	NPC213412
0.8659	High Similarity	NPC477289
0.8642	High Similarity	NPC320514
0.8642	High Similarity	NPC260956
0.8625	High Similarity	NPC18955
0.8621	High Similarity	NPC148964
0.8621	High Similarity	NPC74751
0.8621	High Similarity	NPC474529
0.8608	High Similarity	NPC321514
0.8608	High Similarity	NPC179028
0.8605	High Similarity	NPC60755
0.8605	High Similarity	NPC288833
0.8605	High Similarity	NPC187722
0.8605	High Similarity	NPC228784
0.8605	High Similarity	NPC235884
0.8605	High Similarity	NPC155120
0.8605	High Similarity	NPC470590
0.8605	High Similarity	NPC472149
0.8605	High Similarity	NPC285184
0.8605	High Similarity	NPC324341
0.8605	High Similarity	NPC282616
0.8605	High Similarity	NPC966
0.8605	High Similarity	NPC300351
0.8605	High Similarity	NPC77099
0.8605	High Similarity	NPC52021
0.8605	High Similarity	NPC84319
0.8605	High Similarity	NPC25299
0.8605	High Similarity	NPC71074
0.8605	High Similarity	NPC306541
0.859	High Similarity	NPC309399
0.859	High Similarity	NPC180886
0.8588	High Similarity	NPC112454
0.8588	High Similarity	NPC477973
0.8588	High Similarity	NPC30522
0.8588	High Similarity	NPC474686
0.8571	High Similarity	NPC73064
0.8554	High Similarity	NPC29447
0.8554	High Similarity	NPC469993
0.8537	High Similarity	NPC69279
0.8537	High Similarity	NPC83569
0.8533	High Similarity	NPC286814
0.8523	High Similarity	NPC139570
0.8523	High Similarity	NPC148523
0.8519	High Similarity	NPC477372
0.8506	High Similarity	NPC118519
0.8506	High Similarity	NPC158059
0.8506	High Similarity	NPC307335
0.8506	High Similarity	NPC275809
0.8506	High Similarity	NPC86368
0.8506	High Similarity	NPC229281
0.8506	High Similarity	NPC74855
0.8506	High Similarity	NPC474436
0.8506	High Similarity	NPC263780
0.8506	High Similarity	NPC49776
0.8506	High Similarity	NPC298554
0.8506	High Similarity	NPC136313

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 NPC162632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1753
0.2-0.3	4041
0.3-0.4	2140
0.4-0.5	578
0.5-0.6	229
0.6-0.7	157
0.7-0.8	52
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD7515	Phase 2
0.8621	High Similarity	NPD7748	Approved
0.8588	High Similarity	NPD7285	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7902	Approved
0.8046	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD7614	Phase 1
0.8	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD7900	Approved
0.7976	Intermediate Similarity	NPD3667	Approved
0.7976	Intermediate Similarity	NPD4223	Phase 3
0.7976	Intermediate Similarity	NPD4221	Approved
0.7952	Intermediate Similarity	NPD4695	Discontinued
0.7907	Intermediate Similarity	NPD5329	Approved
0.7907	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6399	Phase 3
0.7816	Intermediate Similarity	NPD6409	Approved
0.7816	Intermediate Similarity	NPD7146	Approved
0.7816	Intermediate Similarity	NPD5330	Approved
0.7816	Intermediate Similarity	NPD6684	Approved
0.7816	Intermediate Similarity	NPD6098	Approved
0.7816	Intermediate Similarity	NPD7334	Approved
0.7816	Intermediate Similarity	NPD7521	Approved
0.7791	Intermediate Similarity	NPD3133	Approved
0.7791	Intermediate Similarity	NPD4197	Approved
0.7791	Intermediate Similarity	NPD3666	Approved
0.7791	Intermediate Similarity	NPD3665	Phase 1
0.7727	Intermediate Similarity	NPD3573	Approved
0.7711	Intermediate Similarity	NPD3617	Approved
0.764	Intermediate Similarity	NPD6903	Approved
0.764	Intermediate Similarity	NPD5737	Approved
0.764	Intermediate Similarity	NPD6672	Approved
0.7619	Intermediate Similarity	NPD7645	Phase 2
0.7614	Intermediate Similarity	NPD5205	Approved
0.7614	Intermediate Similarity	NPD4690	Approved
0.7614	Intermediate Similarity	NPD4688	Approved
0.7614	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD4623	Approved
0.7614	Intermediate Similarity	NPD4693	Phase 3
0.7614	Intermediate Similarity	NPD4138	Approved
0.7614	Intermediate Similarity	NPD3618	Phase 1
0.7614	Intermediate Similarity	NPD4689	Approved
0.7582	Intermediate Similarity	NPD5284	Approved
0.7582	Intermediate Similarity	NPD5281	Approved
0.7556	Intermediate Similarity	NPD6904	Approved
0.7556	Intermediate Similarity	NPD6673	Approved
0.7556	Intermediate Similarity	NPD5328	Approved
0.7556	Intermediate Similarity	NPD6080	Approved
0.7553	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD6084	Phase 2
0.7447	Intermediate Similarity	NPD7732	Phase 3
0.7444	Intermediate Similarity	NPD5208	Approved
0.7436	Intermediate Similarity	NPD4224	Phase 2
0.7416	Intermediate Similarity	NPD5690	Phase 2
0.7416	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5280	Approved
0.7416	Intermediate Similarity	NPD4694	Approved
0.7391	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD8035	Phase 2
0.7391	Intermediate Similarity	NPD6079	Approved
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7375	Intermediate Similarity	NPD4137	Phase 3
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.734	Intermediate Similarity	NPD5695	Phase 3
0.7292	Intermediate Similarity	NPD5696	Approved
0.7284	Intermediate Similarity	NPD4747	Approved
0.7284	Intermediate Similarity	NPD4691	Approved
0.7273	Intermediate Similarity	NPD4788	Approved
0.725	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4139	Approved
0.7241	Intermediate Similarity	NPD4692	Approved
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7209	Intermediate Similarity	NPD4195	Approved
0.7204	Intermediate Similarity	NPD5693	Phase 1
0.7204	Intermediate Similarity	NPD6050	Approved
0.7195	Intermediate Similarity	NPD6081	Approved
0.7195	Intermediate Similarity	NPD4243	Approved
0.7158	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4202	Approved
0.7097	Intermediate Similarity	NPD5207	Approved
0.7097	Intermediate Similarity	NPD5692	Phase 3
0.7053	Intermediate Similarity	NPD6001	Approved
0.7045	Intermediate Similarity	NPD8028	Phase 2
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7024	Intermediate Similarity	NPD4058	Approved
0.7024	Intermediate Similarity	NPD5733	Approved
0.7024	Intermediate Similarity	NPD4785	Approved
0.7024	Intermediate Similarity	NPD4784	Approved
0.7021	Intermediate Similarity	NPD6411	Approved
0.7021	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6979	Remote Similarity	NPD5210	Approved
0.6979	Remote Similarity	NPD4629	Approved
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7339	Approved
0.6941	Remote Similarity	NPD6942	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6915	Remote Similarity	NPD4096	Approved
0.6907	Remote Similarity	NPD5221	Approved
0.6907	Remote Similarity	NPD5222	Approved
0.6907	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6875	Remote Similarity	NPD7341	Phase 2
0.6869	Remote Similarity	NPD7640	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD6404	Discontinued
0.686	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5173	Approved
0.6837	Remote Similarity	NPD4755	Approved
0.6829	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5360	Phase 3
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6824	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4687	Approved
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.6796	Remote Similarity	NPD6412	Phase 2
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6786	Remote Similarity	NPD5276	Approved
0.6771	Remote Similarity	NPD5133	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6744	Remote Similarity	NPD5275	Approved
0.6744	Remote Similarity	NPD4190	Phase 3
0.6742	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD6011	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4518	Approved
0.67	Remote Similarity	NPD5285	Approved
0.67	Remote Similarity	NPD4696	Approved
0.67	Remote Similarity	NPD5286	Approved
0.67	Remote Similarity	NPD4700	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6634	Remote Similarity	NPD5223	Approved
0.6633	Remote Similarity	NPD5654	Approved
0.6591	Remote Similarity	NPD6116	Phase 1
0.6588	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5777	Approved
0.6588	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5224	Approved
0.6569	Remote Similarity	NPD4633	Approved
0.6569	Remote Similarity	NPD5211	Phase 2
0.6569	Remote Similarity	NPD5091	Approved
0.6569	Remote Similarity	NPD5226	Approved
0.6569	Remote Similarity	NPD5225	Approved
0.6559	Remote Similarity	NPD1694	Approved
0.6552	Remote Similarity	NPD8039	Approved
0.6548	Remote Similarity	NPD3698	Phase 2
0.6548	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD6114	Approved
0.6517	Remote Similarity	NPD6697	Approved
0.6517	Remote Similarity	NPD6118	Approved
0.6517	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD5175	Approved
0.6505	Remote Similarity	NPD4754	Approved
0.6505	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5959	Approved
0.6476	Remote Similarity	NPD6614	Approved
0.6463	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6051	Approved
0.6455	Remote Similarity	NPD6868	Approved
0.6447	Remote Similarity	NPD4266	Approved
0.6447	Remote Similarity	NPD3194	Approved
0.6447	Remote Similarity	NPD3195	Phase 2
0.6447	Remote Similarity	NPD3196	Approved
0.6442	Remote Similarity	NPD5141	Approved
0.6437	Remote Similarity	NPD6924	Approved
0.6437	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD5778	Approved
0.6429	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD6858	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