NPASS Compound

Structure

NPC233377 OpenBabel07101718292D 23 24 0 0 1 0 0 0 0 0999 V2000 3.7851 2.3470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1694 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5553 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7966 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0250 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6073 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7326 -0.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6377 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9306 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3313 -1.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4653 1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1973 1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 -0.6399 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 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0553 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0553 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 11 1 1 0 0 0 18 20 1 1 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	4.281
LogD:	3.778
LogS:	-4.705
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	5.317
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.599
MDCK Permeability:	2.8187283533043228e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.1
20% Bioavailability (F20%):	0.099
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	96.01904296875%
Volume Distribution (VD):	0.718
Pgp-substrate:	1.9084630012512207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.343
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	6.063
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.252
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.965
Carcinogencity:	0.053
Eye Corrosion:	0.732
Eye Irritation:	0.886
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC233377

Natural Product ID:	NPC233377
*Common Name:**	14-Deoxycrassin
IUPAC Name:	(1R,4E,8E,12S,13R)-12-hydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-15-one
Synonyms:	14-Deoxycrassin
Standard InCHIKey:	VCLOBFBJUDXQFF-UMFKFABWSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-7-5-8-15(2)10-11-17-13-18(23-19(21)16(17)3)20(4,22)12-6-9-14/h8-9,17-18,22H,3,5-7,10-13H2,1-2,4H3/b14-9+,15-8+/t17-,18-,20+/m1/s1
SMILES:	C/C/1=CCC[C@@](C)([C@H]2C[C@@H](CC/C(=C/CC1)/C)C(=C)C(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512662
PubChem CID:	44560944
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	chinese soft coral	n.a.	PMID[18553926]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30528697]
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644083]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[557187]

☑ 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 NPC233377 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	166
0.1-0.2	1059
0.2-0.3	4674
0.3-0.4	10679
0.4-0.5	13073
0.5-0.6	7345
0.6-0.7	4983
0.7-0.8	687
0.8-0.85	25
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC9868
0.9487	High Similarity	NPC72464
0.9487	High Similarity	NPC243618
0.9487	High Similarity	NPC70424
0.875	High Similarity	NPC474291
0.8734	High Similarity	NPC103634
0.8675	High Similarity	NPC248602
0.8642	High Similarity	NPC11620
0.8571	High Similarity	NPC153805
0.8571	High Similarity	NPC281516
0.8506	High Similarity	NPC71589
0.8488	Intermediate Similarity	NPC470373
0.8488	Intermediate Similarity	NPC470379
0.8471	Intermediate Similarity	NPC307411
0.8434	Intermediate Similarity	NPC137033
0.8375	Intermediate Similarity	NPC469617
0.8372	Intermediate Similarity	NPC474761
0.8372	Intermediate Similarity	NPC51004
0.8372	Intermediate Similarity	NPC476004
0.8353	Intermediate Similarity	NPC474471
0.8353	Intermediate Similarity	NPC202672
0.8353	Intermediate Similarity	NPC227379
0.8333	Intermediate Similarity	NPC164393
0.8276	Intermediate Similarity	NPC12172
0.8276	Intermediate Similarity	NPC208886
0.8276	Intermediate Similarity	NPC30515
0.8276	Intermediate Similarity	NPC184463
0.8214	Intermediate Similarity	NPC21469
0.8182	Intermediate Similarity	NPC212486
0.8182	Intermediate Similarity	NPC179746
0.8182	Intermediate Similarity	NPC476300
0.8182	Intermediate Similarity	NPC81419
0.8182	Intermediate Similarity	NPC475912
0.8118	Intermediate Similarity	NPC122502
0.8095	Intermediate Similarity	NPC14575
0.8095	Intermediate Similarity	NPC474776
0.8095	Intermediate Similarity	NPC196487
0.8095	Intermediate Similarity	NPC474780
0.809	Intermediate Similarity	NPC474035
0.809	Intermediate Similarity	NPC81386
0.8068	Intermediate Similarity	NPC303697
0.8046	Intermediate Similarity	NPC212598
0.8046	Intermediate Similarity	NPC474032
0.8025	Intermediate Similarity	NPC474341
0.8025	Intermediate Similarity	NPC267231
0.8022	Intermediate Similarity	NPC40812
0.8	Intermediate Similarity	NPC149725
0.8	Intermediate Similarity	NPC47958
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC304509
0.8	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC329749
0.8	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC197903
0.8	Intermediate Similarity	NPC272050
0.8	Intermediate Similarity	NPC99395
0.7976	Intermediate Similarity	NPC53867
0.7975	Intermediate Similarity	NPC160540
0.7955	Intermediate Similarity	NPC265856
0.7955	Intermediate Similarity	NPC166554
0.7952	Intermediate Similarity	NPC325031
0.7935	Intermediate Similarity	NPC83895
0.7935	Intermediate Similarity	NPC187761
0.7927	Intermediate Similarity	NPC470239
0.7927	Intermediate Similarity	NPC470244
0.7907	Intermediate Similarity	NPC234038
0.7907	Intermediate Similarity	NPC476015
0.7907	Intermediate Similarity	NPC474949
0.7907	Intermediate Similarity	NPC475019
0.7907	Intermediate Similarity	NPC474762
0.7907	Intermediate Similarity	NPC469483
0.7907	Intermediate Similarity	NPC116575
0.7901	Intermediate Similarity	NPC107668
0.7901	Intermediate Similarity	NPC116177
0.7901	Intermediate Similarity	NPC7563
0.7901	Intermediate Similarity	NPC320630
0.7875	Intermediate Similarity	NPC329852
0.7865	Intermediate Similarity	NPC329952
0.7857	Intermediate Similarity	NPC85772
0.7849	Intermediate Similarity	NPC475053
0.7848	Intermediate Similarity	NPC135703
0.7841	Intermediate Similarity	NPC83423
0.7841	Intermediate Similarity	NPC106040
0.7841	Intermediate Similarity	NPC115179
0.7816	Intermediate Similarity	NPC231889
0.7816	Intermediate Similarity	NPC474765
0.7816	Intermediate Similarity	NPC186148
0.7805	Intermediate Similarity	NPC108816
0.7805	Intermediate Similarity	NPC93763
0.7802	Intermediate Similarity	NPC475659
0.7791	Intermediate Similarity	NPC474369
0.7791	Intermediate Similarity	NPC38468
0.7791	Intermediate Similarity	NPC50362
0.7791	Intermediate Similarity	NPC319795
0.7791	Intermediate Similarity	NPC261380
0.7778	Intermediate Similarity	NPC162205
0.7778	Intermediate Similarity	NPC273579
0.7778	Intermediate Similarity	NPC61863
0.7778	Intermediate Similarity	NPC295204
0.7778	Intermediate Similarity	NPC476049
0.7778	Intermediate Similarity	NPC288240
0.7765	Intermediate Similarity	NPC170377
0.7765	Intermediate Similarity	NPC272814
0.7765	Intermediate Similarity	NPC170286
0.7765	Intermediate Similarity	NPC250315
0.7753	Intermediate Similarity	NPC473448
0.7753	Intermediate Similarity	NPC77337
0.7753	Intermediate Similarity	NPC473619
0.7742	Intermediate Similarity	NPC308567
0.7742	Intermediate Similarity	NPC255592
0.7742	Intermediate Similarity	NPC261377
0.7727	Intermediate Similarity	NPC177629
0.7727	Intermediate Similarity	NPC58219
0.7727	Intermediate Similarity	NPC472008
0.7722	Intermediate Similarity	NPC163003
0.7717	Intermediate Similarity	NPC473859
0.7717	Intermediate Similarity	NPC476315
0.7711	Intermediate Similarity	NPC469690
0.7711	Intermediate Similarity	NPC617
0.7692	Intermediate Similarity	NPC303942
0.7692	Intermediate Similarity	NPC57405
0.7683	Intermediate Similarity	NPC41780
0.7683	Intermediate Similarity	NPC187568
0.7683	Intermediate Similarity	NPC476794
0.7683	Intermediate Similarity	NPC470240
0.7674	Intermediate Similarity	NPC3464
0.7674	Intermediate Similarity	NPC475963
0.7674	Intermediate Similarity	NPC151176
0.7667	Intermediate Similarity	NPC475972
0.7667	Intermediate Similarity	NPC473321
0.7654	Intermediate Similarity	NPC226669
0.7654	Intermediate Similarity	NPC475861
0.7654	Intermediate Similarity	NPC193351
0.7654	Intermediate Similarity	NPC155587
0.7654	Intermediate Similarity	NPC138408
0.7647	Intermediate Similarity	NPC474252
0.7647	Intermediate Similarity	NPC475936
0.764	Intermediate Similarity	NPC295312
0.764	Intermediate Similarity	NPC173926
0.764	Intermediate Similarity	NPC474951
0.764	Intermediate Similarity	NPC92974
0.764	Intermediate Similarity	NPC151770
0.7619	Intermediate Similarity	NPC474510
0.7619	Intermediate Similarity	NPC474981
0.7619	Intermediate Similarity	NPC200446
0.7614	Intermediate Similarity	NPC190753
0.7614	Intermediate Similarity	NPC179659
0.7604	Intermediate Similarity	NPC472747
0.7604	Intermediate Similarity	NPC472750
0.7595	Intermediate Similarity	NPC67183
0.759	Intermediate Similarity	NPC218817
0.759	Intermediate Similarity	NPC11796
0.759	Intermediate Similarity	NPC128276
0.759	Intermediate Similarity	NPC121200
0.759	Intermediate Similarity	NPC471220
0.759	Intermediate Similarity	NPC196653
0.759	Intermediate Similarity	NPC127526
0.759	Intermediate Similarity	NPC471465
0.759	Intermediate Similarity	NPC469495
0.759	Intermediate Similarity	NPC472960
0.7586	Intermediate Similarity	NPC474547
0.7586	Intermediate Similarity	NPC182383
0.7586	Intermediate Similarity	NPC255307
0.7586	Intermediate Similarity	NPC477018
0.7586	Intermediate Similarity	NPC100921
0.7586	Intermediate Similarity	NPC471494
0.7582	Intermediate Similarity	NPC320089
0.7582	Intermediate Similarity	NPC469692
0.7582	Intermediate Similarity	NPC469645
0.7579	Intermediate Similarity	NPC128733
0.7579	Intermediate Similarity	NPC110443
0.7579	Intermediate Similarity	NPC133907
0.7579	Intermediate Similarity	NPC46998
0.7579	Intermediate Similarity	NPC474742
0.7579	Intermediate Similarity	NPC476270
0.7579	Intermediate Similarity	NPC47880
0.7579	Intermediate Similarity	NPC185141
0.7564	Intermediate Similarity	NPC310210
0.7561	Intermediate Similarity	NPC12740
0.7561	Intermediate Similarity	NPC110461
0.7561	Intermediate Similarity	NPC235906
0.7561	Intermediate Similarity	NPC271070
0.7558	Intermediate Similarity	NPC1761
0.7558	Intermediate Similarity	NPC44261
0.7558	Intermediate Similarity	NPC52609
0.7558	Intermediate Similarity	NPC475947
0.7556	Intermediate Similarity	NPC475748
0.7553	Intermediate Similarity	NPC473326
0.7531	Intermediate Similarity	NPC140287
0.7531	Intermediate Similarity	NPC476355
0.7529	Intermediate Similarity	NPC79277
0.7529	Intermediate Similarity	NPC141810
0.7529	Intermediate Similarity	NPC475481
0.7528	Intermediate Similarity	NPC476803
0.7528	Intermediate Similarity	NPC473715
0.7526	Intermediate Similarity	NPC472748
0.75	Intermediate Similarity	NPC469910
0.75	Intermediate Similarity	NPC89128
0.75	Intermediate Similarity	NPC475461
0.75	Intermediate Similarity	NPC474747

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 NPC233377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1470
0.2-0.3	3717
0.3-0.4	2495
0.4-0.5	825
0.5-0.6	365
0.6-0.7	118
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7955	Intermediate Similarity	NPD6698	Approved
0.7955	Intermediate Similarity	NPD46	Approved
0.7791	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7331	Phase 2
0.7283	Intermediate Similarity	NPD7983	Approved
0.7179	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6101	Approved
0.7065	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6435	Approved
0.7024	Intermediate Similarity	NPD8039	Approved
0.701	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7838	Discovery
0.6966	Remote Similarity	NPD7154	Phase 3
0.6962	Remote Similarity	NPD7341	Phase 2
0.6961	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD6422	Discontinued
0.6915	Remote Similarity	NPD6411	Approved
0.6863	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6837	Remote Similarity	NPD4225	Approved
0.6835	Remote Similarity	NPD3197	Phase 1
0.6818	Remote Similarity	NPD5368	Approved
0.6813	Remote Similarity	NPD1694	Approved
0.6809	Remote Similarity	NPD5785	Approved
0.6804	Remote Similarity	NPD7839	Suspended
0.6778	Remote Similarity	NPD5362	Discontinued
0.6742	Remote Similarity	NPD5369	Approved
0.6739	Remote Similarity	NPD5786	Approved
0.6702	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.663	Remote Similarity	NPD5363	Approved
0.663	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5344	Discontinued
0.6484	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4269	Approved
0.6477	Remote Similarity	NPD4756	Discovery
0.6455	Remote Similarity	NPD7115	Discovery
0.6444	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4821	Approved
0.6444	Remote Similarity	NPD4822	Approved
0.6444	Remote Similarity	NPD4819	Approved
0.6444	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD7748	Approved
0.64	Remote Similarity	NPD3172	Approved
0.6389	Remote Similarity	NPD6053	Discontinued
0.6389	Remote Similarity	NPD8297	Approved
0.6383	Remote Similarity	NPD7146	Approved
0.6383	Remote Similarity	NPD7521	Approved
0.6383	Remote Similarity	NPD6684	Approved
0.6383	Remote Similarity	NPD6409	Approved
0.6383	Remote Similarity	NPD7334	Approved
0.6383	Remote Similarity	NPD5330	Approved
0.6381	Remote Similarity	NPD5697	Approved
0.6372	Remote Similarity	NPD8516	Approved
0.6372	Remote Similarity	NPD8515	Approved
0.6372	Remote Similarity	NPD8513	Phase 3
0.6372	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6337	Remote Similarity	NPD7638	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6327	Remote Similarity	NPD6399	Phase 3
0.6321	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD6899	Approved
0.6321	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD3196	Approved
0.6316	Remote Similarity	NPD4266	Approved
0.6316	Remote Similarity	NPD3194	Approved
0.6316	Remote Similarity	NPD3195	Phase 2
0.6293	Remote Similarity	NPD7507	Approved
0.6286	Remote Similarity	NPD5739	Approved
0.6286	Remote Similarity	NPD6675	Approved
0.6286	Remote Similarity	NPD7128	Approved
0.6286	Remote Similarity	NPD6402	Approved
0.6275	Remote Similarity	NPD6648	Approved
0.6275	Remote Similarity	NPD7639	Approved
0.6275	Remote Similarity	NPD7640	Approved
0.6264	Remote Similarity	NPD4252	Approved
0.6263	Remote Similarity	NPD5282	Discontinued
0.6262	Remote Similarity	NPD6013	Approved
0.6262	Remote Similarity	NPD6014	Approved
0.6262	Remote Similarity	NPD6012	Approved
0.6262	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7829	Approved
0.6261	Remote Similarity	NPD7830	Approved
0.6261	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6903	Approved
0.6238	Remote Similarity	NPD7902	Approved
0.6238	Remote Similarity	NPD6084	Phase 2
0.6238	Remote Similarity	NPD6083	Phase 2
0.6237	Remote Similarity	NPD6110	Phase 1
0.6237	Remote Similarity	NPD5331	Approved
0.6237	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD5701	Approved
0.6224	Remote Similarity	NPD5693	Phase 1
0.6224	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD7515	Phase 2
0.6222	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD4271	Approved
0.6204	Remote Similarity	NPD7102	Approved
0.6204	Remote Similarity	NPD7290	Approved
0.6204	Remote Similarity	NPD6883	Approved
0.6203	Remote Similarity	NPD6109	Phase 1
0.6196	Remote Similarity	NPD4790	Discontinued
0.6186	Remote Similarity	NPD5328	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.617	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3133	Approved
0.617	Remote Similarity	NPD3666	Approved
0.617	Remote Similarity	NPD3665	Phase 1
0.6168	Remote Similarity	NPD7320	Approved
0.6147	Remote Similarity	NPD8130	Phase 1
0.6147	Remote Similarity	NPD6617	Approved
0.6147	Remote Similarity	NPD6650	Approved
0.6147	Remote Similarity	NPD6649	Approved
0.6147	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6847	Approved
0.6147	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6319	Approved
0.6134	Remote Similarity	NPD7319	Approved
0.6129	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6373	Approved
0.6102	Remote Similarity	NPD8074	Phase 3
0.6098	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD4695	Discontinued
0.6087	Remote Similarity	NPD8444	Approved
0.6082	Remote Similarity	NPD5737	Approved
0.6082	Remote Similarity	NPD6672	Approved
0.6075	Remote Similarity	NPD6412	Phase 2
0.6055	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD4249	Approved
0.6042	Remote Similarity	NPD5279	Phase 3
0.6024	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD7909	Approved
0.6018	Remote Similarity	NPD6009	Approved
0.6017	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4786	Approved
0.598	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5222	Approved
0.598	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD4251	Approved
0.5979	Remote Similarity	NPD4250	Approved
0.5976	Remote Similarity	NPD368	Approved
0.5966	Remote Similarity	NPD8448	Approved
0.5962	Remote Similarity	NPD4696	Approved
0.5962	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5286	Approved
0.5957	Remote Similarity	NPD4221	Approved
0.5957	Remote Similarity	NPD4223	Phase 3
0.5948	Remote Similarity	NPD5983	Phase 2
0.5941	Remote Similarity	NPD7900	Approved
0.5941	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6274	Approved
0.5922	Remote Similarity	NPD4755	Approved
0.5922	Remote Similarity	NPD5173	Approved
0.5921	Remote Similarity	NPD29	Approved
0.5921	Remote Similarity	NPD28	Approved
0.5921	Remote Similarity	NPD6927	Phase 3
0.592	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5208	Approved
0.5905	Remote Similarity	NPD5223	Approved
0.5902	Remote Similarity	NPD7260	Phase 2
0.59	Remote Similarity	NPD5281	Approved
0.59	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5284	Approved
0.59	Remote Similarity	NPD7637	Suspended
0.5897	Remote Similarity	NPD3728	Approved
0.5897	Remote Similarity	NPD3730	Approved
0.5893	Remote Similarity	NPD8133	Approved
0.5888	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD3704	Approved
0.5877	Remote Similarity	NPD6317	Approved
0.5876	Remote Similarity	NPD6098	Approved
0.5876	Remote Similarity	NPD4623	Approved
0.5876	Remote Similarity	NPD4519	Discontinued
0.5876	Remote Similarity	NPD5690	Phase 2
0.587	Remote Similarity	NPD3732	Approved
0.5867	Remote Similarity	NPD3173	Approved
0.5859	Remote Similarity	NPD5370	Suspended
0.5859	Remote Similarity	NPD6080	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