NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	408.32
Volume:	459.651
LogP:	6.136
LogD:	4.266
LogS:	-3.285
# Rotatable Bonds:	17
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	3.544
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	2.409529588476289e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.326
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.752
Plasma Protein Binding (PPB):	98.96378326416016%
Volume Distribution (VD):	0.937
Pgp-substrate:	0.9153429269790649%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.333
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	5.259
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.454
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.947
Carcinogencity:	0.146
Eye Corrosion:	0.024
Eye Irritation:	0.233
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC477785

Natural Product ID:	NPC477785
*Common Name:**	(4S,5R,6R)-4,5,6-trihydroxy-6-[(Z)-nonadec-10-enyl]cyclohex-2-en-1-one
IUPAC Name:	(4S,5R,6R)-4,5,6-trihydroxy-6-[(Z)-nonadec-10-enyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	WSLKVXXQIATOBK-OKXJYCGPSA-N
Standard InCHI:	InChI=1S/C25H44O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-25(29)23(27)20-19-22(26)24(25)28/h9-10,19-20,22,24,26,28-29H,2-8,11-18,21H2,1H3/b10-9-/t22-,24+,25-/m0/s1
SMILES:	CCCCCCCC/C=C\CCCCCCCCC[C@]1([C@@H]([C@H](C=CC1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122184837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO33552	Pleiogynium timoriense	Species	Anacardiaceae	Eukaryota	bark	n.a.	n.a.	PMID[26132421]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	700	nM	PMID[26132421]

☑ 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 NPC477785 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	182
0.1-0.2	1243
0.2-0.3	5376
0.3-0.4	11633
0.4-0.5	14324
0.5-0.6	6778
0.6-0.7	2753
0.7-0.8	382
0.8-0.85	17
0.85-0.9	1
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477786
1.0	High Similarity	NPC477784
0.9351	High Similarity	NPC231739
0.8795	High Similarity	NPC187529
0.8395	Intermediate Similarity	NPC478122
0.8372	Intermediate Similarity	NPC472007
0.8295	Intermediate Similarity	NPC477684
0.8256	Intermediate Similarity	NPC472009
0.8095	Intermediate Similarity	NPC275766
0.8068	Intermediate Similarity	NPC472008
0.8049	Intermediate Similarity	NPC471061
0.7975	Intermediate Similarity	NPC107848
0.7927	Intermediate Similarity	NPC474197
0.7912	Intermediate Similarity	NPC469645
0.7912	Intermediate Similarity	NPC469692
0.7889	Intermediate Similarity	NPC471399
0.7841	Intermediate Similarity	NPC196381
0.7831	Intermediate Similarity	NPC473536
0.7831	Intermediate Similarity	NPC97173
0.7831	Intermediate Similarity	NPC82666
0.7826	Intermediate Similarity	NPC121825
0.7812	Intermediate Similarity	NPC39996
0.7802	Intermediate Similarity	NPC476705
0.7802	Intermediate Similarity	NPC142838
0.7766	Intermediate Similarity	NPC266842
0.7765	Intermediate Similarity	NPC470947
0.7765	Intermediate Similarity	NPC470946
0.7765	Intermediate Similarity	NPC470945
0.7753	Intermediate Similarity	NPC471738
0.7738	Intermediate Similarity	NPC475994
0.7738	Intermediate Similarity	NPC192006
0.7727	Intermediate Similarity	NPC79573
0.7692	Intermediate Similarity	NPC137163
0.7692	Intermediate Similarity	NPC166554
0.7692	Intermediate Similarity	NPC265856
0.7674	Intermediate Similarity	NPC67254
0.7674	Intermediate Similarity	NPC474980
0.7647	Intermediate Similarity	NPC113363
0.7619	Intermediate Similarity	NPC281296
0.7586	Intermediate Similarity	NPC475690
0.7586	Intermediate Similarity	NPC7414
0.7579	Intermediate Similarity	NPC20066
0.7579	Intermediate Similarity	NPC40812
0.7561	Intermediate Similarity	NPC275098
0.7558	Intermediate Similarity	NPC472948
0.7556	Intermediate Similarity	NPC179659
0.7551	Intermediate Similarity	NPC104161
0.7551	Intermediate Similarity	NPC469980
0.7551	Intermediate Similarity	NPC118902
0.7529	Intermediate Similarity	NPC121200
0.7528	Intermediate Similarity	NPC261380
0.7528	Intermediate Similarity	NPC125290
0.7528	Intermediate Similarity	NPC11804
0.7528	Intermediate Similarity	NPC77971
0.7526	Intermediate Similarity	NPC185141
0.7526	Intermediate Similarity	NPC128733
0.7526	Intermediate Similarity	NPC110443
0.7526	Intermediate Similarity	NPC133907
0.7526	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC469464
0.75	Intermediate Similarity	NPC161045
0.75	Intermediate Similarity	NPC477708
0.75	Intermediate Similarity	NPC187761
0.75	Intermediate Similarity	NPC300584
0.75	Intermediate Similarity	NPC83895
0.75	Intermediate Similarity	NPC469853
0.7474	Intermediate Similarity	NPC473291
0.7473	Intermediate Similarity	NPC53454
0.7473	Intermediate Similarity	NPC476708
0.7473	Intermediate Similarity	NPC87189
0.7473	Intermediate Similarity	NPC476707
0.7473	Intermediate Similarity	NPC228415
0.7473	Intermediate Similarity	NPC476706
0.7471	Intermediate Similarity	NPC47031
0.7471	Intermediate Similarity	NPC470298
0.747	Intermediate Similarity	NPC122244
0.7468	Intermediate Similarity	NPC472072
0.7449	Intermediate Similarity	NPC87351
0.7447	Intermediate Similarity	NPC78159
0.7447	Intermediate Similarity	NPC472977
0.7447	Intermediate Similarity	NPC472976
0.7447	Intermediate Similarity	NPC65829
0.7444	Intermediate Similarity	NPC316426
0.7444	Intermediate Similarity	NPC194417
0.7444	Intermediate Similarity	NPC261721
0.7444	Intermediate Similarity	NPC315395
0.7444	Intermediate Similarity	NPC476982
0.7442	Intermediate Similarity	NPC19900
0.7419	Intermediate Similarity	NPC475441
0.7419	Intermediate Similarity	NPC146852
0.7416	Intermediate Similarity	NPC469809
0.7412	Intermediate Similarity	NPC476007
0.74	Intermediate Similarity	NPC469852
0.74	Intermediate Similarity	NPC472615
0.7396	Intermediate Similarity	NPC471694
0.7386	Intermediate Similarity	NPC279186
0.7386	Intermediate Similarity	NPC38796
0.7386	Intermediate Similarity	NPC158411
0.7386	Intermediate Similarity	NPC85772
0.7386	Intermediate Similarity	NPC474252
0.7381	Intermediate Similarity	NPC474885
0.7381	Intermediate Similarity	NPC199445
0.7381	Intermediate Similarity	NPC60718
0.7375	Intermediate Similarity	NPC26500
0.7375	Intermediate Similarity	NPC106613
0.7375	Intermediate Similarity	NPC99619
0.7374	Intermediate Similarity	NPC111323
0.7374	Intermediate Similarity	NPC475945
0.7374	Intermediate Similarity	NPC475871
0.7374	Intermediate Similarity	NPC472755
0.7374	Intermediate Similarity	NPC311612
0.7368	Intermediate Similarity	NPC476245
0.7363	Intermediate Similarity	NPC23622
0.7363	Intermediate Similarity	NPC72513
0.7356	Intermediate Similarity	NPC115418
0.7353	Intermediate Similarity	NPC87335
0.7353	Intermediate Similarity	NPC214644
0.7347	Intermediate Similarity	NPC470184
0.7347	Intermediate Similarity	NPC472753
0.7347	Intermediate Similarity	NPC474742
0.734	Intermediate Similarity	NPC474736
0.734	Intermediate Similarity	NPC61275
0.7333	Intermediate Similarity	NPC255174
0.7333	Intermediate Similarity	NPC474853
0.7333	Intermediate Similarity	NPC179006
0.7333	Intermediate Similarity	NPC28887
0.7327	Intermediate Similarity	NPC266514
0.7326	Intermediate Similarity	NPC218817
0.7326	Intermediate Similarity	NPC11796
0.732	Intermediate Similarity	NPC161855
0.732	Intermediate Similarity	NPC306908
0.732	Intermediate Similarity	NPC255592
0.732	Intermediate Similarity	NPC261377
0.732	Intermediate Similarity	NPC308567
0.7317	Intermediate Similarity	NPC291062
0.7317	Intermediate Similarity	NPC94743
0.7312	Intermediate Similarity	NPC473448
0.7312	Intermediate Similarity	NPC316228
0.7308	Intermediate Similarity	NPC66108
0.7303	Intermediate Similarity	NPC251475
0.7303	Intermediate Similarity	NPC16488
0.7303	Intermediate Similarity	NPC62214
0.7303	Intermediate Similarity	NPC169941
0.73	Intermediate Similarity	NPC472616
0.73	Intermediate Similarity	NPC220964
0.73	Intermediate Similarity	NPC475676
0.73	Intermediate Similarity	NPC472756
0.73	Intermediate Similarity	NPC160843
0.7294	Intermediate Similarity	NPC279537
0.7294	Intermediate Similarity	NPC469514
0.7294	Intermediate Similarity	NPC256640
0.7294	Intermediate Similarity	NPC205615
0.7294	Intermediate Similarity	NPC16279
0.7292	Intermediate Similarity	NPC93271
0.7292	Intermediate Similarity	NPC135576
0.7283	Intermediate Similarity	NPC471791
0.7283	Intermediate Similarity	NPC476803
0.7283	Intermediate Similarity	NPC471793
0.7273	Intermediate Similarity	NPC286229
0.7273	Intermediate Similarity	NPC474747
0.7273	Intermediate Similarity	NPC112868
0.7273	Intermediate Similarity	NPC149371
0.7273	Intermediate Similarity	NPC472754
0.7263	Intermediate Similarity	NPC469632
0.7263	Intermediate Similarity	NPC477241
0.7262	Intermediate Similarity	NPC160540
0.7253	Intermediate Similarity	NPC262026
0.7253	Intermediate Similarity	NPC469483
0.7253	Intermediate Similarity	NPC94666
0.7253	Intermediate Similarity	NPC469910
0.7253	Intermediate Similarity	NPC472974
0.7241	Intermediate Similarity	NPC473980
0.7241	Intermediate Similarity	NPC473981
0.7241	Intermediate Similarity	NPC164308
0.7241	Intermediate Similarity	NPC201225
0.7234	Intermediate Similarity	NPC111114
0.7234	Intermediate Similarity	NPC472978
0.7234	Intermediate Similarity	NPC172101
0.7234	Intermediate Similarity	NPC261607
0.7234	Intermediate Similarity	NPC230623
0.7234	Intermediate Similarity	NPC116726
0.7234	Intermediate Similarity	NPC300312
0.7228	Intermediate Similarity	NPC166607
0.7222	Intermediate Similarity	NPC31086
0.7222	Intermediate Similarity	NPC243618
0.7222	Intermediate Similarity	NPC70424
0.7222	Intermediate Similarity	NPC476412
0.7216	Intermediate Similarity	NPC474938
0.7216	Intermediate Similarity	NPC470522
0.7216	Intermediate Similarity	NPC473161
0.7216	Intermediate Similarity	NPC474785
0.7216	Intermediate Similarity	NPC135685
0.7216	Intermediate Similarity	NPC239895
0.7215	Intermediate Similarity	NPC7029
0.7212	Intermediate Similarity	NPC317107
0.7209	Intermediate Similarity	NPC272267
0.7204	Intermediate Similarity	NPC473100
0.72	Intermediate Similarity	NPC4620
0.72	Intermediate Similarity	NPC247957
0.72	Intermediate Similarity	NPC475050

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 NPC477785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1845
0.2-0.3	3837
0.3-0.4	2212
0.4-0.5	738
0.5-0.6	275
0.6-0.7	61
0.7-0.8	12
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
0.7931	Intermediate Similarity	NPD5363	Approved
0.7586	Intermediate Similarity	NPD4269	Approved
0.7586	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7356	Intermediate Similarity	NPD4252	Approved
0.7273	Intermediate Similarity	NPD5369	Approved
0.7253	Intermediate Similarity	NPD5786	Approved
0.725	Intermediate Similarity	NPD7331	Phase 2
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6110	Phase 1
0.7089	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5282	Discontinued
0.7053	Intermediate Similarity	NPD7983	Approved
0.7011	Intermediate Similarity	NPD4756	Discovery
0.7	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3197	Phase 1
0.6979	Remote Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6966	Remote Similarity	NPD4819	Approved
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD4820	Approved
0.6947	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD6698	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7154	Phase 3
0.6881	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD5210	Approved
0.6829	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3704	Approved
0.6827	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6371	Approved
0.6778	Remote Similarity	NPD4695	Discontinued
0.6774	Remote Similarity	NPD1696	Phase 3
0.6765	Remote Similarity	NPD5211	Phase 2
0.6742	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD4271	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6707	Remote Similarity	NPD7341	Phase 2
0.6701	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6635	Remote Similarity	NPD5141	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.66	Remote Similarity	NPD7839	Suspended
0.6593	Remote Similarity	NPD5368	Approved
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5285	Approved
0.6569	Remote Similarity	NPD5286	Approved
0.6569	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD6411	Approved
0.6526	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6435	Approved
0.6442	Remote Similarity	NPD5224	Approved
0.6442	Remote Similarity	NPD5225	Approved
0.6442	Remote Similarity	NPD5226	Approved
0.6442	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5221	Approved
0.6436	Remote Similarity	NPD5222	Approved
0.6436	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7838	Discovery
0.6422	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6381	Remote Similarity	NPD5174	Approved
0.6381	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD4755	Approved
0.6373	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6354	Remote Similarity	NPD4623	Approved
0.6354	Remote Similarity	NPD4519	Discontinued
0.6354	Remote Similarity	NPD3618	Phase 1
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5690	Phase 2
0.6346	Remote Similarity	NPD5223	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.6316	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6277	Remote Similarity	NPD3667	Approved
0.6275	Remote Similarity	NPD4697	Phase 3
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD4700	Approved
0.622	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8297	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.62	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD7637	Suspended
0.6196	Remote Similarity	NPD3732	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6174	Remote Similarity	NPD4522	Approved
0.6163	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD4730	Approved
0.6147	Remote Similarity	NPD4729	Approved
0.6146	Remote Similarity	NPD4197	Approved
0.6146	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD368	Approved
0.614	Remote Similarity	NPD7500	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6617	Approved
0.6122	Remote Similarity	NPD4251	Approved
0.6122	Remote Similarity	NPD4250	Approved
0.6121	Remote Similarity	NPD6319	Approved
0.6121	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6054	Approved
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6102	Remote Similarity	NPD7642	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6082	Remote Similarity	NPD1694	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6068	Remote Similarity	NPD8513	Phase 3
0.6068	Remote Similarity	NPD8515	Approved
0.6068	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD8516	Approved
0.6044	Remote Similarity	NPD8264	Approved
0.6044	Remote Similarity	NPD8039	Approved
0.6036	Remote Similarity	NPD5247	Approved
0.6036	Remote Similarity	NPD5251	Approved
0.6036	Remote Similarity	NPD5248	Approved
0.6036	Remote Similarity	NPD5250	Approved
0.6036	Remote Similarity	NPD5249	Phase 3
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD4694	Approved
0.602	Remote Similarity	NPD5280	Approved
0.6018	Remote Similarity	NPD4632	Approved
0.6017	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.5982	Remote Similarity	NPD5215	Approved
0.5982	Remote Similarity	NPD5216	Approved
0.5982	Remote Similarity	NPD5217	Approved
0.598	Remote Similarity	NPD6399	Phase 3
0.598	Remote Similarity	NPD4202	Approved
0.5963	Remote Similarity	NPD4768	Approved
0.5963	Remote Similarity	NPD4767	Approved
0.5938	Remote Similarity	NPD4221	Approved
0.5938	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD4223	Phase 3
0.5932	Remote Similarity	NPD6016	Approved
0.5932	Remote Similarity	NPD6015	Approved
0.5926	Remote Similarity	NPD4754	Approved
0.5922	Remote Similarity	NPD7748	Approved
0.5918	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7492	Approved
0.5909	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD7902	Approved
0.59	Remote Similarity	NPD5737	Approved
0.59	Remote Similarity	NPD4518	Approved
0.59	Remote Similarity	NPD6672	Approved
0.5895	Remote Similarity	NPD7514	Phase 3
0.5895	Remote Similarity	NPD7332	Phase 2
0.5893	Remote Similarity	NPD5169	Approved
0.5893	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5135	Approved
0.5882	Remote Similarity	NPD7623	Phase 3
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD5988	Approved
0.5882	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5284	Approved
0.5875	Remote Similarity	NPD4266	Approved
0.5875	Remote Similarity	NPD3195	Phase 2
0.5875	Remote Similarity	NPD3196	Approved
0.5875	Remote Similarity	NPD3194	Approved
0.5872	Remote Similarity	NPD1237	Approved
0.5868	Remote Similarity	NPD6616	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