NPASS Compound

Structure

NPC469867 OpenBabel07101718182D 24 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 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 0.0000 -2.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 2 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 1 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.26
Volume:	375.808
LogP:	3.411
LogD:	3.253
LogS:	-4.522
# Rotatable Bonds:	9
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	4.249
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.591
MDCK Permeability:	2.0248980945325457e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	57.136375427246094%
Volume Distribution (VD):	1.134
Pgp-substrate:	51.597572326660156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	7.635
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.045
Carcinogencity:	0.025
Eye Corrosion:	0.005
Eye Irritation:	0.05
Respiratory Toxicity:	0.19

Download Data

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

Natural Product: NPC469867

Natural Product ID:	NPC469867
*Common Name:**	Negombatodiol
IUPAC Name:	methyl (2R,3R,6R)-8-(2,2-dimethyl-6-methylidenecyclohexyl)-3,6-dihydroxy-2,6-dimethyloctanoate
Synonyms:	Negombatodiol
Standard InCHIKey:	OKRBMWPDGMFNRO-CYXPSIDGSA-N
Standard InCHI:	InChI=1S/C20H36O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5,23)13-10-17(21)15(2)18(22)24-6/h15-17,21,23H,1,7-13H2,2-6H3/t15-,16?,17-,20-/m1/s1
SMILES:	COC(=O)[C@@H]([C@@H](CC[C@@](CCC1C(=C)CCCC1(C)C)(O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223693
PubChem CID:	46939592
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	formosan	n.a.	PMID[20718475]
NPO4211	Negombata corticata	Species	Latrunculiidae	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
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[509939]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[509939]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[509939]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[509939]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[509939]

☑ 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 NPC469867 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	169
0.1-0.2	1523
0.2-0.3	5825
0.3-0.4	14872
0.4-0.5	7446
0.5-0.6	7150
0.6-0.7	5176
0.7-0.8	493
0.8-0.85	27
0.85-0.9	12
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC476986
0.9324	High Similarity	NPC470905
0.9091	High Similarity	NPC475395
0.9091	High Similarity	NPC476984
0.9054	High Similarity	NPC476985
0.9054	High Similarity	NPC475744
0.9054	High Similarity	NPC474316
0.8846	High Similarity	NPC474605
0.8846	High Similarity	NPC476292
0.8642	High Similarity	NPC476104
0.859	High Similarity	NPC476265
0.859	High Similarity	NPC274522
0.8519	High Similarity	NPC471344
0.85	High Similarity	NPC476983
0.8481	Intermediate Similarity	NPC117960
0.8481	Intermediate Similarity	NPC14044
0.8481	Intermediate Similarity	NPC172309
0.8462	Intermediate Similarity	NPC82488
0.8462	Intermediate Similarity	NPC308545
0.8442	Intermediate Similarity	NPC474433
0.8442	Intermediate Similarity	NPC122847
0.8415	Intermediate Similarity	NPC262085
0.8378	Intermediate Similarity	NPC91369
0.8333	Intermediate Similarity	NPC77001
0.8333	Intermediate Similarity	NPC469866
0.8333	Intermediate Similarity	NPC471342
0.8333	Intermediate Similarity	NPC253618
0.8313	Intermediate Similarity	NPC134197
0.8272	Intermediate Similarity	NPC476100
0.825	Intermediate Similarity	NPC476988
0.8205	Intermediate Similarity	NPC476264
0.8205	Intermediate Similarity	NPC476325
0.8194	Intermediate Similarity	NPC476330
0.8108	Intermediate Similarity	NPC290445
0.8108	Intermediate Similarity	NPC36616
0.8101	Intermediate Similarity	NPC321514
0.8077	Intermediate Similarity	NPC152754
0.8077	Intermediate Similarity	NPC469514
0.8077	Intermediate Similarity	NPC476601
0.8077	Intermediate Similarity	NPC476987
0.8077	Intermediate Similarity	NPC59602
0.8026	Intermediate Similarity	NPC72343
0.8025	Intermediate Similarity	NPC327002
0.8	Intermediate Similarity	NPC183374
0.8	Intermediate Similarity	NPC255176
0.8	Intermediate Similarity	NPC211162
0.7976	Intermediate Similarity	NPC475181
0.7976	Intermediate Similarity	NPC476982
0.7976	Intermediate Similarity	NPC73038
0.7952	Intermediate Similarity	NPC471343
0.7907	Intermediate Similarity	NPC57954
0.7907	Intermediate Similarity	NPC213832
0.7889	Intermediate Similarity	NPC253586
0.7875	Intermediate Similarity	NPC247783
0.7875	Intermediate Similarity	NPC269543
0.7875	Intermediate Similarity	NPC121200
0.7865	Intermediate Similarity	NPC205173
0.7857	Intermediate Similarity	NPC201655
0.7857	Intermediate Similarity	NPC329738
0.7841	Intermediate Similarity	NPC471902
0.7841	Intermediate Similarity	NPC473690
0.7841	Intermediate Similarity	NPC199543
0.7841	Intermediate Similarity	NPC287118
0.7831	Intermediate Similarity	NPC471037
0.7831	Intermediate Similarity	NPC243347
0.7821	Intermediate Similarity	NPC46610
0.7821	Intermediate Similarity	NPC330016
0.7821	Intermediate Similarity	NPC18819
0.7805	Intermediate Similarity	NPC223330
0.7805	Intermediate Similarity	NPC209318
0.7805	Intermediate Similarity	NPC475951
0.7791	Intermediate Similarity	NPC56413
0.7791	Intermediate Similarity	NPC471900
0.7791	Intermediate Similarity	NPC146937
0.7778	Intermediate Similarity	NPC132824
0.7778	Intermediate Similarity	NPC254996
0.7778	Intermediate Similarity	NPC327674
0.7778	Intermediate Similarity	NPC476438
0.7778	Intermediate Similarity	NPC268502
0.7778	Intermediate Similarity	NPC192999
0.7765	Intermediate Similarity	NPC324063
0.7765	Intermediate Similarity	NPC185638
0.7765	Intermediate Similarity	NPC80590
0.7765	Intermediate Similarity	NPC475753
0.7765	Intermediate Similarity	NPC475007
0.7765	Intermediate Similarity	NPC322159
0.7753	Intermediate Similarity	NPC469982
0.775	Intermediate Similarity	NPC238227
0.775	Intermediate Similarity	NPC281296
0.7738	Intermediate Similarity	NPC263974
0.7738	Intermediate Similarity	NPC120158
0.7738	Intermediate Similarity	NPC475193
0.7733	Intermediate Similarity	NPC469868
0.7727	Intermediate Similarity	NPC155120
0.7727	Intermediate Similarity	NPC324341
0.7727	Intermediate Similarity	NPC475416
0.7727	Intermediate Similarity	NPC471901
0.7727	Intermediate Similarity	NPC966
0.7727	Intermediate Similarity	NPC36491
0.7727	Intermediate Similarity	NPC282616
0.7727	Intermediate Similarity	NPC471588
0.7727	Intermediate Similarity	NPC288833
0.7727	Intermediate Similarity	NPC228784
0.7727	Intermediate Similarity	NPC6255
0.7722	Intermediate Similarity	NPC199445
0.7717	Intermediate Similarity	NPC108371
0.7711	Intermediate Similarity	NPC123880
0.7711	Intermediate Similarity	NPC471159
0.7701	Intermediate Similarity	NPC116146
0.7701	Intermediate Similarity	NPC24772
0.7692	Intermediate Similarity	NPC167145
0.7683	Intermediate Similarity	NPC103634
0.7674	Intermediate Similarity	NPC477926
0.7674	Intermediate Similarity	NPC158141
0.7674	Intermediate Similarity	NPC173089
0.7674	Intermediate Similarity	NPC96496
0.7674	Intermediate Similarity	NPC269360
0.7674	Intermediate Similarity	NPC33768
0.7674	Intermediate Similarity	NPC264005
0.7671	Intermediate Similarity	NPC474552
0.7667	Intermediate Similarity	NPC210214
0.7654	Intermediate Similarity	NPC239098
0.7654	Intermediate Similarity	NPC476810
0.7647	Intermediate Similarity	NPC76333
0.764	Intermediate Similarity	NPC118490
0.7625	Intermediate Similarity	NPC474447
0.7619	Intermediate Similarity	NPC239308
0.7619	Intermediate Similarity	NPC477373
0.7619	Intermediate Similarity	NPC312480
0.7619	Intermediate Similarity	NPC245866
0.7619	Intermediate Similarity	NPC69469
0.7614	Intermediate Similarity	NPC172361
0.7614	Intermediate Similarity	NPC130278
0.7614	Intermediate Similarity	NPC169933
0.7614	Intermediate Similarity	NPC86372
0.7609	Intermediate Similarity	NPC474793
0.7609	Intermediate Similarity	NPC164349
0.7609	Intermediate Similarity	NPC174663
0.7595	Intermediate Similarity	NPC71152
0.759	Intermediate Similarity	NPC232625
0.759	Intermediate Similarity	NPC14203
0.759	Intermediate Similarity	NPC229584
0.759	Intermediate Similarity	NPC473420
0.7586	Intermediate Similarity	NPC1753
0.7586	Intermediate Similarity	NPC254572
0.7586	Intermediate Similarity	NPC48824
0.7586	Intermediate Similarity	NPC229407
0.7586	Intermediate Similarity	NPC474511
0.7586	Intermediate Similarity	NPC250687
0.7586	Intermediate Similarity	NPC294480
0.7586	Intermediate Similarity	NPC104560
0.7586	Intermediate Similarity	NPC183546
0.7582	Intermediate Similarity	NPC201657
0.7582	Intermediate Similarity	NPC223169
0.7582	Intermediate Similarity	NPC98874
0.7582	Intermediate Similarity	NPC120708
0.7582	Intermediate Similarity	NPC471153
0.7561	Intermediate Similarity	NPC28319
0.7561	Intermediate Similarity	NPC19841
0.7561	Intermediate Similarity	NPC263951
0.7558	Intermediate Similarity	NPC187545
0.7558	Intermediate Similarity	NPC198761
0.7558	Intermediate Similarity	NPC472505
0.7558	Intermediate Similarity	NPC2783
0.7558	Intermediate Similarity	NPC12774
0.7558	Intermediate Similarity	NPC325594
0.7558	Intermediate Similarity	NPC212843
0.7558	Intermediate Similarity	NPC473226
0.7558	Intermediate Similarity	NPC70661
0.7558	Intermediate Similarity	NPC202394
0.7556	Intermediate Similarity	NPC47853
0.7556	Intermediate Similarity	NPC6818
0.7556	Intermediate Similarity	NPC148964
0.7556	Intermediate Similarity	NPC184006
0.7556	Intermediate Similarity	NPC191412
0.7556	Intermediate Similarity	NPC169751
0.7556	Intermediate Similarity	NPC23621
0.7556	Intermediate Similarity	NPC78580
0.7556	Intermediate Similarity	NPC114159
0.7556	Intermediate Similarity	NPC222047
0.7556	Intermediate Similarity	NPC272635
0.7531	Intermediate Similarity	NPC66105
0.7529	Intermediate Similarity	NPC165064
0.7529	Intermediate Similarity	NPC130966
0.7528	Intermediate Similarity	NPC154101
0.7528	Intermediate Similarity	NPC472814
0.7528	Intermediate Similarity	NPC177037
0.7528	Intermediate Similarity	NPC250753
0.7528	Intermediate Similarity	NPC471747
0.7527	Intermediate Similarity	NPC477655
0.7527	Intermediate Similarity	NPC35239
0.7527	Intermediate Similarity	NPC474718
0.75	Intermediate Similarity	NPC106112
0.75	Intermediate Similarity	NPC61543
0.75	Intermediate Similarity	NPC89225
0.75	Intermediate Similarity	NPC474419
0.75	Intermediate Similarity	NPC127689
0.75	Intermediate Similarity	NPC145143
0.75	Intermediate Similarity	NPC270768
0.75	Intermediate Similarity	NPC60718

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 NPC469867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2207
0.2-0.3	3731
0.3-0.4	1969
0.4-0.5	567
0.5-0.6	352
0.6-0.7	154
0.7-0.8	3
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
0.7727	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7253	Intermediate Similarity	NPD5779	Approved
0.7253	Intermediate Similarity	NPD5778	Approved
0.7253	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7128	Intermediate Similarity	NPD6084	Phase 2
0.7128	Intermediate Similarity	NPD6083	Phase 2
0.7093	Intermediate Similarity	NPD6435	Approved
0.7059	Intermediate Similarity	NPD5368	Approved
0.7042	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4788	Approved
0.6989	Remote Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD6402	Approved
0.697	Remote Similarity	NPD5739	Approved
0.697	Remote Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD7637	Suspended
0.6947	Remote Similarity	NPD7902	Approved
0.6932	Remote Similarity	NPD4786	Approved
0.6915	Remote Similarity	NPD5695	Phase 3
0.6915	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6116	Phase 1
0.6897	Remote Similarity	NPD4270	Approved
0.6897	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD4819	Approved
0.686	Remote Similarity	NPD4820	Approved
0.686	Remote Similarity	NPD4822	Approved
0.686	Remote Similarity	NPD4821	Approved
0.6848	Remote Similarity	NPD5785	Approved
0.6832	Remote Similarity	NPD6881	Approved
0.6832	Remote Similarity	NPD6899	Approved
0.6832	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7320	Approved
0.6818	Remote Similarity	NPD5362	Discontinued
0.6818	Remote Similarity	NPD7154	Phase 3
0.6809	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD6117	Approved
0.6778	Remote Similarity	NPD6409	Approved
0.6778	Remote Similarity	NPD5786	Approved
0.6778	Remote Similarity	NPD6684	Approved
0.6778	Remote Similarity	NPD5330	Approved
0.6778	Remote Similarity	NPD7521	Approved
0.6778	Remote Similarity	NPD7146	Approved
0.6778	Remote Similarity	NPD7334	Approved
0.6774	Remote Similarity	NPD7983	Approved
0.6765	Remote Similarity	NPD6373	Approved
0.6765	Remote Similarity	NPD6372	Approved
0.6747	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3133	Approved
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD3666	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6733	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD5697	Approved
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD5696	Approved
0.6699	Remote Similarity	NPD6883	Approved
0.6699	Remote Similarity	NPD7102	Approved
0.6699	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6650	Approved
0.6635	Remote Similarity	NPD8130	Phase 1
0.6635	Remote Similarity	NPD6869	Approved
0.6635	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6649	Approved
0.6635	Remote Similarity	NPD6847	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6903	Approved
0.663	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD5737	Approved
0.663	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4268	Approved
0.6628	Remote Similarity	NPD6118	Approved
0.6628	Remote Similarity	NPD6114	Approved
0.6628	Remote Similarity	NPD6697	Approved
0.6628	Remote Similarity	NPD4271	Approved
0.6628	Remote Similarity	NPD6115	Approved
0.6602	Remote Similarity	NPD6012	Approved
0.6602	Remote Similarity	NPD6014	Approved
0.6602	Remote Similarity	NPD6013	Approved
0.6598	Remote Similarity	NPD4755	Approved
0.6596	Remote Similarity	NPD5284	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6593	Remote Similarity	NPD5279	Phase 3
0.6593	Remote Similarity	NPD3618	Phase 1
0.6579	Remote Similarity	NPD3198	Approved
0.6571	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD6882	Approved
0.6559	Remote Similarity	NPD5328	Approved
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6531	Remote Similarity	NPD7638	Approved
0.6526	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD8133	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6495	Remote Similarity	NPD7839	Suspended
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD7525	Registered
0.6477	Remote Similarity	NPD4695	Discontinued
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3702	Approved
0.6471	Remote Similarity	NPD8039	Approved
0.6465	Remote Similarity	NPD7639	Approved
0.6465	Remote Similarity	NPD4700	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6456	Remote Similarity	NPD7909	Approved
0.6444	Remote Similarity	NPD6695	Phase 3
0.6421	Remote Similarity	NPD6079	Approved
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6386	Remote Similarity	NPD4245	Approved
0.6386	Remote Similarity	NPD4244	Approved
0.6383	Remote Similarity	NPD6080	Approved
0.6383	Remote Similarity	NPD6904	Approved
0.6383	Remote Similarity	NPD6673	Approved
0.6383	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7341	Phase 2
0.6375	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3668	Phase 3
0.6364	Remote Similarity	NPD7645	Phase 2
0.6341	Remote Similarity	NPD229	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5211	Phase 2
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.631	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6081	Approved
0.631	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5777	Approved
0.6306	Remote Similarity	NPD6319	Approved
0.6304	Remote Similarity	NPD5329	Approved
0.6304	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4224	Phase 2
0.6296	Remote Similarity	NPD7331	Phase 2
0.6292	Remote Similarity	NPD7509	Discontinued
0.6292	Remote Similarity	NPD6930	Phase 2
0.6292	Remote Similarity	NPD6931	Approved
0.6286	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.6265	Remote Similarity	NPD3698	Phase 2
0.6265	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5331	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3197	Phase 1
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4802	Phase 2
0.625	Remote Similarity	NPD3732	Approved
0.625	Remote Similarity	NPD4238	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6237	Remote Similarity	NPD6422	Discontinued
0.6228	Remote Similarity	NPD7492	Approved
0.6226	Remote Similarity	NPD4634	Approved
0.6224	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4790	Discontinued
0.6216	Remote Similarity	NPD7101	Approved
0.6216	Remote Similarity	NPD7100	Approved
0.6214	Remote Similarity	NPD5141	Approved
0.6204	Remote Similarity	NPD4632	Approved
0.6196	Remote Similarity	NPD4197	Approved
0.619	Remote Similarity	NPD4789	Approved
0.6182	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6929	Approved
0.6174	Remote Similarity	NPD6616	Approved
0.617	Remote Similarity	NPD3573	Approved
0.617	Remote Similarity	NPD4251	Approved
0.617	Remote Similarity	NPD4250	Approved
0.617	Remote Similarity	NPD7524	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