NPASS Compound

Structure

CID186385 OpenBabel06191715562D 23 24 0 0 1 0 0 0 0 0999 V2000 -4.9883 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9883 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1569 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 0.4800 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 0.8314 -1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 17 14 1 6 0 0 0 17 18 1 0 0 0 0 18 21 1 1 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	359.057
LogP:	6.691
LogD:	4.77
LogS:	-3.175
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	3.461
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.774
MDCK Permeability:	1.8164641005569138e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	99.0204849243164%
Volume Distribution (VD):	8.484
Pgp-substrate:	1.257685899734497%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.819
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.462
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	4.697
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.275
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.711
Carcinogencity:	0.048
Eye Corrosion:	0.015
Eye Irritation:	0.708
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC186385

Natural Product ID:	NPC186385
*Common Name:**	2-((1S,6S)-3-Methyl-6-(Prop-1-En-2-Yl)Cyclohex-2-Enyl)-5-Pentylbenzene-1,3-Diol
IUPAC Name:	2-[(1S,6S)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	QHMBSVQNZZTUGM-MSOLQXFVSA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m1/s1
SMILES:	CCCCCc1cc(c([C@H]2C=C(C)CC[C@@H]2C(=C)C)c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3810140
PubChem CID:	36688143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19122328]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19159272]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159272]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10027	Cannabis indica	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8716	Uvariopsis solheidii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5773	Anaerobic eubacterium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9421	Platismatia glauca	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10824	Pterogyne nitens	Species	Fabaceae	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	2
Ki	3

Activity Type	# Activity
Individual Protein	3
ORGANISM	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	842.0	nM	PMID[506263]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	203.0	nM	PMID[506265]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	842.0	nM	PMID[506265]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[506264]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[506264]

☑ 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 NPC186385 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	307
0.1-0.2	1628
0.2-0.3	4365
0.3-0.4	13588
0.4-0.5	6137
0.5-0.6	8610
0.6-0.7	6194
0.7-0.8	1542
0.8-0.85	192
0.85-0.9	89
0.9-0.95	35
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299568
0.9619	High Similarity	NPC319803
0.9615	High Similarity	NPC224527
0.9604	High Similarity	NPC37802
0.951	High Similarity	NPC201662
0.951	High Similarity	NPC99836
0.951	High Similarity	NPC12640
0.9505	High Similarity	NPC227458
0.9505	High Similarity	NPC218879
0.9505	High Similarity	NPC244513
0.9434	High Similarity	NPC23804
0.9423	High Similarity	NPC33728
0.9423	High Similarity	NPC19808
0.9417	High Similarity	NPC232523
0.9417	High Similarity	NPC204901
0.9417	High Similarity	NPC158253
0.9327	High Similarity	NPC174981
0.9259	High Similarity	NPC84999
0.9259	High Similarity	NPC246760
0.9159	High Similarity	NPC166995
0.9118	High Similarity	NPC166313
0.9118	High Similarity	NPC192032
0.9118	High Similarity	NPC137415
0.9118	High Similarity	NPC24407
0.9118	High Similarity	NPC11280
0.9118	High Similarity	NPC147310
0.9118	High Similarity	NPC294186
0.9074	High Similarity	NPC263753
0.9074	High Similarity	NPC117846
0.9029	High Similarity	NPC53051
0.9029	High Similarity	NPC24404
0.9029	High Similarity	NPC313030
0.9029	High Similarity	NPC85479
0.9029	High Similarity	NPC106396
0.9029	High Similarity	NPC71002
0.9029	High Similarity	NPC242342
0.9029	High Similarity	NPC302219
0.9029	High Similarity	NPC146798
0.9029	High Similarity	NPC168303
0.9029	High Similarity	NPC222522
0.9029	High Similarity	NPC94351
0.9029	High Similarity	NPC249828
0.902	High Similarity	NPC10588
0.902	High Similarity	NPC166761
0.9009	High Similarity	NPC206
0.9009	High Similarity	NPC9592
0.9009	High Similarity	NPC48781
0.8972	High Similarity	NPC224870
0.8942	High Similarity	NPC241891
0.8942	High Similarity	NPC102216
0.8932	High Similarity	NPC72947
0.8932	High Similarity	NPC284011
0.8899	High Similarity	NPC261343
0.8889	High Similarity	NPC165770
0.8889	High Similarity	NPC476632
0.8889	High Similarity	NPC4493
0.8889	High Similarity	NPC225679
0.8857	High Similarity	NPC246056
0.8857	High Similarity	NPC134829
0.8835	High Similarity	NPC72729
0.8829	High Similarity	NPC115808
0.8824	High Similarity	NPC79241
0.8824	High Similarity	NPC6597
0.8818	High Similarity	NPC107240
0.8807	High Similarity	NPC473521
0.8807	High Similarity	NPC43525
0.8774	High Similarity	NPC118286
0.8774	High Similarity	NPC39097
0.8774	High Similarity	NPC248904
0.8774	High Similarity	NPC109691
0.8774	High Similarity	NPC470700
0.8774	High Similarity	NPC39664
0.8774	High Similarity	NPC302681
0.875	High Similarity	NPC100340
0.875	High Similarity	NPC143659
0.875	High Similarity	NPC470760
0.8725	High Similarity	NPC259512
0.8725	High Similarity	NPC312132
0.8716	High Similarity	NPC54373
0.8707	High Similarity	NPC96940
0.8692	High Similarity	NPC305603
0.8692	High Similarity	NPC54844
0.8692	High Similarity	NPC66834
0.8692	High Similarity	NPC61033
0.8684	High Similarity	NPC69006
0.8679	High Similarity	NPC474839
0.8679	High Similarity	NPC117115
0.8673	High Similarity	NPC144343
0.8673	High Similarity	NPC190514
0.8621	High Similarity	NPC122175
0.8614	High Similarity	NPC295295
0.8611	High Similarity	NPC61885
0.8611	High Similarity	NPC63698
0.8598	High Similarity	NPC21594
0.8596	High Similarity	NPC191866
0.8596	High Similarity	NPC184302
0.8585	High Similarity	NPC119860
0.8585	High Similarity	NPC475225
0.8585	High Similarity	NPC30506
0.8571	High Similarity	NPC252105
0.8571	High Similarity	NPC477685
0.8558	High Similarity	NPC33675
0.8558	High Similarity	NPC299762
0.8558	High Similarity	NPC80027
0.8545	High Similarity	NPC469912
0.8545	High Similarity	NPC151537
0.8534	High Similarity	NPC39029
0.8532	High Similarity	NPC202647
0.8519	High Similarity	NPC151477
0.8505	High Similarity	NPC292452
0.8505	High Similarity	NPC47284
0.8491	Intermediate Similarity	NPC471228
0.8491	Intermediate Similarity	NPC235762
0.8482	Intermediate Similarity	NPC249270
0.8475	Intermediate Similarity	NPC139774
0.8475	Intermediate Similarity	NPC174729
0.8468	Intermediate Similarity	NPC228452
0.8462	Intermediate Similarity	NPC291789
0.8455	Intermediate Similarity	NPC132720
0.8448	Intermediate Similarity	NPC24125
0.8448	Intermediate Similarity	NPC218753
0.844	Intermediate Similarity	NPC306295
0.8426	Intermediate Similarity	NPC469913
0.8426	Intermediate Similarity	NPC53740
0.8421	Intermediate Similarity	NPC277588
0.8421	Intermediate Similarity	NPC69261
0.8421	Intermediate Similarity	NPC33270
0.8407	Intermediate Similarity	NPC808
0.8378	Intermediate Similarity	NPC470770
0.8378	Intermediate Similarity	NPC266937
0.8349	Intermediate Similarity	NPC320439
0.8348	Intermediate Similarity	NPC154030
0.8347	Intermediate Similarity	NPC38604
0.8347	Intermediate Similarity	NPC211179
0.8333	Intermediate Similarity	NPC471350
0.8333	Intermediate Similarity	NPC91204
0.8333	Intermediate Similarity	NPC150624
0.8333	Intermediate Similarity	NPC231150
0.8333	Intermediate Similarity	NPC111723
0.8333	Intermediate Similarity	NPC237517
0.8319	Intermediate Similarity	NPC224342
0.8318	Intermediate Similarity	NPC168393
0.8305	Intermediate Similarity	NPC77789
0.8305	Intermediate Similarity	NPC18128
0.8304	Intermediate Similarity	NPC62867
0.8304	Intermediate Similarity	NPC250323
0.8304	Intermediate Similarity	NPC177962
0.8304	Intermediate Similarity	NPC302371
0.8302	Intermediate Similarity	NPC275053
0.8302	Intermediate Similarity	NPC248396
0.8302	Intermediate Similarity	NPC48730
0.8302	Intermediate Similarity	NPC248573
0.8302	Intermediate Similarity	NPC129373
0.8302	Intermediate Similarity	NPC161571
0.8302	Intermediate Similarity	NPC174911
0.8288	Intermediate Similarity	NPC168657
0.8288	Intermediate Similarity	NPC475018
0.8286	Intermediate Similarity	NPC152097
0.8279	Intermediate Similarity	NPC472795
0.8279	Intermediate Similarity	NPC472796
0.8276	Intermediate Similarity	NPC217174
0.8276	Intermediate Similarity	NPC85895
0.8276	Intermediate Similarity	NPC137294
0.8264	Intermediate Similarity	NPC32715
0.8264	Intermediate Similarity	NPC257947
0.8264	Intermediate Similarity	NPC66331
0.8264	Intermediate Similarity	NPC98200
0.8261	Intermediate Similarity	NPC50521
0.8261	Intermediate Similarity	NPC221549
0.8261	Intermediate Similarity	NPC244816
0.8261	Intermediate Similarity	NPC304510
0.8261	Intermediate Similarity	NPC172219
0.8261	Intermediate Similarity	NPC320864
0.8257	Intermediate Similarity	NPC155072
0.8257	Intermediate Similarity	NPC310456
0.8252	Intermediate Similarity	NPC210497
0.8252	Intermediate Similarity	NPC94139
0.8252	Intermediate Similarity	NPC306884
0.8252	Intermediate Similarity	NPC162314
0.8252	Intermediate Similarity	NPC147284
0.8252	Intermediate Similarity	NPC3358
0.825	Intermediate Similarity	NPC105031
0.8246	Intermediate Similarity	NPC53906
0.8246	Intermediate Similarity	NPC232165
0.8241	Intermediate Similarity	NPC272029
0.8241	Intermediate Similarity	NPC315936
0.8235	Intermediate Similarity	NPC192
0.823	Intermediate Similarity	NPC162113
0.823	Intermediate Similarity	NPC62546
0.8224	Intermediate Similarity	NPC80800
0.8224	Intermediate Similarity	NPC12221
0.822	Intermediate Similarity	NPC237667
0.8214	Intermediate Similarity	NPC260323
0.8214	Intermediate Similarity	NPC176279
0.8214	Intermediate Similarity	NPC77772
0.8208	Intermediate Similarity	NPC260775
0.8205	Intermediate Similarity	NPC223451
0.8205	Intermediate Similarity	NPC3239
0.8205	Intermediate Similarity	NPC282255
0.8198	Intermediate Similarity	NPC58865

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 NPC186385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	1010
0.2-0.3	1543
0.3-0.4	3029
0.4-0.5	1756
0.5-0.6	1105
0.6-0.7	351
0.7-0.8	43
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4750	Phase 3
0.875	High Similarity	NPD940	Approved
0.875	High Similarity	NPD846	Approved
0.8725	High Similarity	NPD288	Approved
0.8707	High Similarity	NPD4749	Approved
0.8627	High Similarity	NPD844	Approved
0.8333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1242	Phase 1
0.8211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD3020	Approved
0.8142	Intermediate Similarity	NPD7635	Approved
0.8131	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD845	Approved
0.7984	Intermediate Similarity	NPD4625	Phase 3
0.7925	Intermediate Similarity	NPD2859	Approved
0.7925	Intermediate Similarity	NPD2860	Approved
0.7876	Intermediate Similarity	NPD3022	Approved
0.7876	Intermediate Similarity	NPD3021	Approved
0.7857	Intermediate Similarity	NPD2342	Discontinued
0.783	Intermediate Similarity	NPD2934	Approved
0.783	Intermediate Similarity	NPD2933	Approved
0.783	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD1809	Phase 2
0.7634	Intermediate Similarity	NPD6100	Approved
0.7634	Intermediate Similarity	NPD6099	Approved
0.7623	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.7611	Intermediate Similarity	NPD1444	Approved
0.7611	Intermediate Similarity	NPD1445	Approved
0.7565	Intermediate Similarity	NPD1792	Phase 2
0.7537	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6671	Approved
0.7459	Intermediate Similarity	NPD2932	Approved
0.7438	Intermediate Similarity	NPD3091	Approved
0.7426	Intermediate Similarity	NPD9093	Approved
0.7353	Intermediate Similarity	NPD9089	Approved
0.7339	Intermediate Similarity	NPD3092	Approved
0.7317	Intermediate Similarity	NPD4059	Approved
0.7317	Intermediate Similarity	NPD3019	Approved
0.7311	Intermediate Similarity	NPD2234	Approved
0.7311	Intermediate Similarity	NPD2228	Approved
0.7311	Intermediate Similarity	NPD2229	Approved
0.7308	Intermediate Similarity	NPD111	Approved
0.7302	Intermediate Similarity	NPD6696	Suspended
0.7295	Intermediate Similarity	NPD1548	Phase 1
0.7293	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3094	Phase 2
0.7222	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD422	Phase 1
0.7177	Intermediate Similarity	NPD4626	Approved
0.7154	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9273	Approved
0.7132	Intermediate Similarity	NPD2861	Phase 2
0.7131	Intermediate Similarity	NPD7340	Approved
0.7122	Intermediate Similarity	NPD7390	Discontinued
0.7107	Intermediate Similarity	NPD497	Approved
0.7097	Intermediate Similarity	NPD4093	Discontinued
0.7063	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD858	Approved
0.7054	Intermediate Similarity	NPD599	Approved
0.7054	Intermediate Similarity	NPD602	Approved
0.7054	Intermediate Similarity	NPD859	Approved
0.7043	Intermediate Similarity	NPD9500	Approved
0.704	Intermediate Similarity	NPD1751	Approved
0.704	Intermediate Similarity	NPD2286	Discontinued
0.704	Intermediate Similarity	NPD3095	Discontinued
0.7025	Intermediate Similarity	NPD495	Approved
0.7025	Intermediate Similarity	NPD498	Approved
0.7025	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1398	Phase 1
0.7025	Intermediate Similarity	NPD496	Approved
0.7016	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD5303	Approved
0.7015	Intermediate Similarity	NPD4097	Suspended
0.7008	Intermediate Similarity	NPD2233	Approved
0.7008	Intermediate Similarity	NPD2232	Approved
0.7008	Intermediate Similarity	NPD2230	Approved
0.6992	Remote Similarity	NPD943	Approved
0.6992	Remote Similarity	NPD1613	Approved
0.6992	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD1470	Approved
0.6977	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1791	Approved
0.6967	Remote Similarity	NPD1793	Approved
0.6944	Remote Similarity	NPD9094	Approved
0.6912	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4589	Approved
0.6897	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2568	Approved
0.6889	Remote Similarity	NPD1607	Approved
0.6885	Remote Similarity	NPD5283	Phase 1
0.6884	Remote Similarity	NPD970	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7330	Discontinued
0.687	Remote Similarity	NPD3028	Approved
0.687	Remote Similarity	NPD5736	Approved
0.687	Remote Similarity	NPD3018	Phase 2
0.6861	Remote Similarity	NPD5404	Approved
0.6861	Remote Similarity	NPD5406	Approved
0.6861	Remote Similarity	NPD5408	Approved
0.6861	Remote Similarity	NPD5405	Approved
0.686	Remote Similarity	NPD228	Approved
0.6855	Remote Similarity	NPD7636	Approved
0.685	Remote Similarity	NPD1981	Approved
0.685	Remote Similarity	NPD1980	Approved
0.685	Remote Similarity	NPD1983	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6825	Remote Similarity	NPD5691	Approved
0.6794	Remote Similarity	NPD2195	Approved
0.6794	Remote Similarity	NPD2194	Approved
0.6786	Remote Similarity	NPD3892	Phase 2
0.6774	Remote Similarity	NPD709	Approved
0.6772	Remote Similarity	NPD1778	Approved
0.6761	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1608	Approved
0.6742	Remote Similarity	NPD3637	Approved
0.6742	Remote Similarity	NPD3635	Approved
0.6742	Remote Similarity	NPD3636	Approved
0.6741	Remote Similarity	NPD1240	Approved
0.6741	Remote Similarity	NPD4060	Phase 1
0.6719	Remote Similarity	NPD3026	Approved
0.6719	Remote Similarity	NPD3023	Approved
0.6718	Remote Similarity	NPD1133	Approved
0.6718	Remote Similarity	NPD1129	Approved
0.6718	Remote Similarity	NPD1135	Approved
0.6718	Remote Similarity	NPD1134	Approved
0.6718	Remote Similarity	NPD1131	Approved
0.6716	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD9608	Approved
0.6695	Remote Similarity	NPD9610	Approved
0.6694	Remote Similarity	NPD9614	Approved
0.6694	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9618	Approved
0.6693	Remote Similarity	NPD3025	Approved
0.6693	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3024	Approved
0.6693	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2982	Phase 2
0.6692	Remote Similarity	NPD4659	Approved
0.6692	Remote Similarity	NPD2605	Approved
0.6692	Remote Similarity	NPD2606	Approved
0.6692	Remote Similarity	NPD2983	Phase 2
0.6692	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD9377	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9379	Approved
0.6642	Remote Similarity	NPD5155	Approved
0.6642	Remote Similarity	NPD5156	Approved
0.6641	Remote Similarity	NPD2668	Approved
0.6641	Remote Similarity	NPD1283	Approved
0.6641	Remote Similarity	NPD2667	Approved
0.6639	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3620	Phase 2
0.6618	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1555	Discontinued
0.6615	Remote Similarity	NPD2981	Phase 2
0.6615	Remote Similarity	NPD9269	Phase 2
0.6614	Remote Similarity	NPD1759	Phase 1
0.6613	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD74	Approved
0.6612	Remote Similarity	NPD9266	Approved
0.6612	Remote Similarity	NPD2684	Approved
0.6597	Remote Similarity	NPD2532	Approved
0.6597	Remote Similarity	NPD2534	Approved
0.6597	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2533	Approved
0.6596	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3268	Approved
0.6591	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4103	Phase 2
0.6591	Remote Similarity	NPD1164	Approved
0.6589	Remote Similarity	NPD3143	Discontinued
0.6589	Remote Similarity	NPD3496	Discontinued
0.6587	Remote Similarity	NPD9493	Approved
0.6583	Remote Similarity	NPD968	Approved
0.6581	Remote Similarity	NPD1616	Discontinued
0.6571	Remote Similarity	NPD4726	Approved
0.6571	Remote Similarity	NPD4721	Approved
0.6571	Remote Similarity	NPD5763	Approved
0.6571	Remote Similarity	NPD5762	Approved
0.6571	Remote Similarity	NPD4725	Approved
0.6569	Remote Similarity	NPD5124	Phase 1
0.6569	Remote Similarity	NPD9087	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