NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.44
LogD:	1.62
LogS:	-3.687
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	5.048
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083
MDCK Permeability:	5.574443639488891e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	68.74610900878906%
Volume Distribution (VD):	0.278
Pgp-substrate:	25.3789005279541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.354
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	5.756
Half-life (T1/2):	0.511

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.538
Carcinogencity:	0.757
Eye Corrosion:	0.862
Eye Irritation:	0.783
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: NPC74685

Natural Product ID:	NPC74685
*Common Name:**	SMAWCSOVJJHIOI-DDIVZENXSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Terrecyclic Acid A
Standard InCHIKey:	SMAWCSOVJJHIOI-DDIVZENXSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m0/s1
SMILES:	C=C1C(=O)C[C@H]2[C@@H]3CC[C@H](C(=O)O)[C@]12CC3(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469079
PubChem CID:	339487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10600.0	nM	PMID[478625]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	24100.0	nM	PMID[478625]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	14700.0	nM	PMID[478625]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	40.7	%	PMID[478625]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	16.0	%	PMID[478625]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	43.7	%	PMID[478625]

☑ 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 NPC74685 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	171
0.1-0.2	1891
0.2-0.3	11365
0.3-0.4	13102
0.4-0.5	7438
0.5-0.6	6277
0.6-0.7	2238
0.7-0.8	208
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC475932
0.8519	High Similarity	NPC142649
0.8442	Intermediate Similarity	NPC212661
0.8442	Intermediate Similarity	NPC471035
0.8193	Intermediate Similarity	NPC6247
0.8158	Intermediate Similarity	NPC177826
0.8077	Intermediate Similarity	NPC20466
0.8072	Intermediate Similarity	NPC473038
0.8049	Intermediate Similarity	NPC65350
0.8049	Intermediate Similarity	NPC472740
0.8025	Intermediate Similarity	NPC477372
0.8	Intermediate Similarity	NPC477371
0.8	Intermediate Similarity	NPC192744
0.7975	Intermediate Similarity	NPC66105
0.7949	Intermediate Similarity	NPC132064
0.7922	Intermediate Similarity	NPC161187
0.7922	Intermediate Similarity	NPC244708
0.7922	Intermediate Similarity	NPC330659
0.7895	Intermediate Similarity	NPC235586
0.7895	Intermediate Similarity	NPC18543
0.7887	Intermediate Similarity	NPC270042
0.7875	Intermediate Similarity	NPC321690
0.7857	Intermediate Similarity	NPC94531
0.7857	Intermediate Similarity	NPC311702
0.7857	Intermediate Similarity	NPC123319
0.7857	Intermediate Similarity	NPC29447
0.7848	Intermediate Similarity	NPC246445
0.7805	Intermediate Similarity	NPC147066
0.7805	Intermediate Similarity	NPC38350
0.7805	Intermediate Similarity	NPC232625
0.7805	Intermediate Similarity	NPC201912
0.775	Intermediate Similarity	NPC68828
0.775	Intermediate Similarity	NPC169389
0.775	Intermediate Similarity	NPC106078
0.7738	Intermediate Similarity	NPC209882
0.7733	Intermediate Similarity	NPC263161
0.7722	Intermediate Similarity	NPC39362
0.7711	Intermediate Similarity	NPC238991
0.7711	Intermediate Similarity	NPC302661
0.7711	Intermediate Similarity	NPC133391
0.7711	Intermediate Similarity	NPC477270
0.7711	Intermediate Similarity	NPC477271
0.7711	Intermediate Similarity	NPC129080
0.7711	Intermediate Similarity	NPC260956
0.7711	Intermediate Similarity	NPC320514
0.7711	Intermediate Similarity	NPC477269
0.7692	Intermediate Similarity	NPC472813
0.7683	Intermediate Similarity	NPC26139
0.7683	Intermediate Similarity	NPC279667
0.7654	Intermediate Similarity	NPC476810
0.7619	Intermediate Similarity	NPC470015
0.7619	Intermediate Similarity	NPC83569
0.7619	Intermediate Similarity	NPC168188
0.7619	Intermediate Similarity	NPC69279
0.7619	Intermediate Similarity	NPC477373
0.7619	Intermediate Similarity	NPC102197
0.76	Intermediate Similarity	NPC103734
0.7586	Intermediate Similarity	NPC56413
0.7564	Intermediate Similarity	NPC472309
0.7561	Intermediate Similarity	NPC471475
0.7561	Intermediate Similarity	NPC158846
0.7558	Intermediate Similarity	NPC80590
0.7532	Intermediate Similarity	NPC475952
0.7531	Intermediate Similarity	NPC238227
0.7531	Intermediate Similarity	NPC97377
0.7529	Intermediate Similarity	NPC164577
0.75	Intermediate Similarity	NPC472311
0.75	Intermediate Similarity	NPC476795
0.75	Intermediate Similarity	NPC258153
0.75	Intermediate Similarity	NPC476458
0.75	Intermediate Similarity	NPC262043
0.7471	Intermediate Similarity	NPC136948
0.747	Intermediate Similarity	NPC164999
0.7468	Intermediate Similarity	NPC52667
0.7468	Intermediate Similarity	NPC248567
0.7468	Intermediate Similarity	NPC321017
0.7467	Intermediate Similarity	NPC469791
0.7442	Intermediate Similarity	NPC11711
0.7442	Intermediate Similarity	NPC201655
0.7439	Intermediate Similarity	NPC74410
0.7439	Intermediate Similarity	NPC63020
0.7412	Intermediate Similarity	NPC271784
0.7412	Intermediate Similarity	NPC118800
0.7412	Intermediate Similarity	NPC97913
0.7412	Intermediate Similarity	NPC175410
0.7412	Intermediate Similarity	NPC167103
0.7412	Intermediate Similarity	NPC245866
0.7407	Intermediate Similarity	NPC180886
0.7403	Intermediate Similarity	NPC476629
0.7403	Intermediate Similarity	NPC290445
0.7403	Intermediate Similarity	NPC36616
0.7391	Intermediate Similarity	NPC472941
0.7391	Intermediate Similarity	NPC456
0.7391	Intermediate Similarity	NPC470387
0.7386	Intermediate Similarity	NPC117122
0.7386	Intermediate Similarity	NPC183374
0.7386	Intermediate Similarity	NPC211162
0.7381	Intermediate Similarity	NPC278459
0.7356	Intermediate Similarity	NPC70661
0.7356	Intermediate Similarity	NPC186975
0.7356	Intermediate Similarity	NPC472869
0.7349	Intermediate Similarity	NPC472490
0.7349	Intermediate Similarity	NPC201459
0.7349	Intermediate Similarity	NPC215843
0.7349	Intermediate Similarity	NPC118987
0.7349	Intermediate Similarity	NPC263951
0.734	Intermediate Similarity	NPC287833
0.7333	Intermediate Similarity	NPC198242
0.7333	Intermediate Similarity	NPC211403
0.7333	Intermediate Similarity	NPC250753
0.7333	Intermediate Similarity	NPC204341
0.7326	Intermediate Similarity	NPC472865
0.7326	Intermediate Similarity	NPC19849
0.7326	Intermediate Similarity	NPC320801
0.7326	Intermediate Similarity	NPC146683
0.7326	Intermediate Similarity	NPC472864
0.7326	Intermediate Similarity	NPC238197
0.7326	Intermediate Similarity	NPC165064
0.7317	Intermediate Similarity	NPC137547
0.7317	Intermediate Similarity	NPC165711
0.7312	Intermediate Similarity	NPC43747
0.7303	Intermediate Similarity	NPC116146
0.7303	Intermediate Similarity	NPC24772
0.7303	Intermediate Similarity	NPC473039
0.7294	Intermediate Similarity	NPC100297
0.7294	Intermediate Similarity	NPC193347
0.7294	Intermediate Similarity	NPC170985
0.7284	Intermediate Similarity	NPC201263
0.7284	Intermediate Similarity	NPC155441
0.7283	Intermediate Similarity	NPC266431
0.7283	Intermediate Similarity	NPC255809
0.7283	Intermediate Similarity	NPC241156
0.7283	Intermediate Similarity	NPC37646
0.7273	Intermediate Similarity	NPC236618
0.7273	Intermediate Similarity	NPC167877
0.7273	Intermediate Similarity	NPC476409
0.7273	Intermediate Similarity	NPC60120
0.7273	Intermediate Similarity	NPC96496
0.7263	Intermediate Similarity	NPC71706
0.7263	Intermediate Similarity	NPC475867
0.7263	Intermediate Similarity	NPC270155
0.7262	Intermediate Similarity	NPC170038
0.7262	Intermediate Similarity	NPC472478
0.7253	Intermediate Similarity	NPC294263
0.725	Intermediate Similarity	NPC279241
0.725	Intermediate Similarity	NPC35656
0.725	Intermediate Similarity	NPC36310
0.7241	Intermediate Similarity	NPC294438
0.7241	Intermediate Similarity	NPC469948
0.7241	Intermediate Similarity	NPC269638
0.7241	Intermediate Similarity	NPC264317
0.7241	Intermediate Similarity	NPC8571
0.7241	Intermediate Similarity	NPC76518
0.7215	Intermediate Similarity	NPC163020
0.7215	Intermediate Similarity	NPC91369
0.7215	Intermediate Similarity	NPC108131
0.7209	Intermediate Similarity	NPC471037
0.7209	Intermediate Similarity	NPC469561
0.7209	Intermediate Similarity	NPC291320
0.7209	Intermediate Similarity	NPC107253
0.7209	Intermediate Similarity	NPC471036
0.7209	Intermediate Similarity	NPC105803
0.7209	Intermediate Similarity	NPC477852
0.7204	Intermediate Similarity	NPC243525
0.7204	Intermediate Similarity	NPC40765
0.7204	Intermediate Similarity	NPC3772
0.7204	Intermediate Similarity	NPC125622
0.7191	Intermediate Similarity	NPC474719
0.7191	Intermediate Similarity	NPC48824
0.7191	Intermediate Similarity	NPC472870
0.7191	Intermediate Similarity	NPC254572
0.7191	Intermediate Similarity	NPC250687
0.7191	Intermediate Similarity	NPC229407
0.7179	Intermediate Similarity	NPC470956
0.7176	Intermediate Similarity	NPC471898
0.7176	Intermediate Similarity	NPC103754
0.7176	Intermediate Similarity	NPC90055
0.7176	Intermediate Similarity	NPC474484
0.7174	Intermediate Similarity	NPC470386
0.7174	Intermediate Similarity	NPC166906
0.7174	Intermediate Similarity	NPC470385
0.7174	Intermediate Similarity	NPC475118
0.7174	Intermediate Similarity	NPC56525
0.716	Intermediate Similarity	NPC199316
0.716	Intermediate Similarity	NPC18819
0.716	Intermediate Similarity	NPC102313
0.716	Intermediate Similarity	NPC46610
0.7159	Intermediate Similarity	NPC155011
0.7159	Intermediate Similarity	NPC2783
0.7159	Intermediate Similarity	NPC55309
0.7159	Intermediate Similarity	NPC28252
0.7159	Intermediate Similarity	NPC229717
0.7159	Intermediate Similarity	NPC471042
0.7159	Intermediate Similarity	NPC12774
0.7159	Intermediate Similarity	NPC475007
0.7158	Intermediate Similarity	NPC51370
0.7143	Intermediate Similarity	NPC7232
0.7143	Intermediate Similarity	NPC274996
0.7143	Intermediate Similarity	NPC230064
0.7143	Intermediate Similarity	NPC473986

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 NPC74685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2594
0.2-0.3	4218
0.3-0.4	1448
0.4-0.5	355
0.5-0.6	195
0.6-0.7	152
0.7-0.8	7
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
0.7564	Intermediate Similarity	NPD6081	Approved
0.7412	Intermediate Similarity	NPD4788	Approved
0.7368	Intermediate Similarity	NPD4224	Phase 2
0.7294	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD4223	Phase 3
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3617	Approved
0.7159	Intermediate Similarity	NPD5690	Phase 2
0.7143	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7126	Intermediate Similarity	NPD4197	Approved
0.7053	Intermediate Similarity	NPD5696	Approved
0.7045	Intermediate Similarity	NPD5329	Approved
0.7013	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6903	Approved
0.6977	Remote Similarity	NPD4139	Approved
0.6977	Remote Similarity	NPD4692	Approved
0.6966	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4138	Approved
0.6966	Remote Similarity	NPD5205	Approved
0.6966	Remote Similarity	NPD5280	Approved
0.6966	Remote Similarity	NPD4693	Phase 3
0.6966	Remote Similarity	NPD4688	Approved
0.6966	Remote Similarity	NPD4689	Approved
0.6966	Remote Similarity	NPD4694	Approved
0.6966	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD6079	Approved
0.6932	Remote Similarity	NPD4786	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3133	Approved
0.6932	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6915	Remote Similarity	NPD4629	Approved
0.6915	Remote Similarity	NPD5210	Approved
0.6915	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD3667	Approved
0.6882	Remote Similarity	NPD6399	Phase 3
0.6867	Remote Similarity	NPD3702	Approved
0.6848	Remote Similarity	NPD5207	Approved
0.6842	Remote Similarity	NPD7614	Phase 1
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6813	Remote Similarity	NPD5208	Approved
0.6778	Remote Similarity	NPD7146	Approved
0.6778	Remote Similarity	NPD7521	Approved
0.6778	Remote Similarity	NPD3618	Phase 1
0.6778	Remote Similarity	NPD6684	Approved
0.6778	Remote Similarity	NPD5330	Approved
0.6778	Remote Similarity	NPD6098	Approved
0.6778	Remote Similarity	NPD5279	Phase 3
0.6778	Remote Similarity	NPD7334	Approved
0.6778	Remote Similarity	NPD6409	Approved
0.6774	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD8035	Phase 2
0.6771	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD5360	Phase 3
0.675	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4195	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6739	Remote Similarity	NPD6904	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6632	Remote Similarity	NPD6001	Approved
0.663	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5173	Approved
0.6596	Remote Similarity	NPD6050	Approved
0.6596	Remote Similarity	NPD5694	Approved
0.6596	Remote Similarity	NPD5693	Phase 1
0.6588	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD4789	Approved
0.6585	Remote Similarity	NPD4691	Approved
0.6585	Remote Similarity	NPD4747	Approved
0.6575	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5697	Approved
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5133	Approved
0.6526	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6512	Remote Similarity	NPD6116	Phase 1
0.6506	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4758	Discontinued
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD5091	Approved
0.6495	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD4096	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD6404	Discontinued
0.6465	Remote Similarity	NPD5286	Approved
0.6463	Remote Similarity	NPD4137	Phase 3
0.6463	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3698	Phase 2
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD6114	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6697	Approved
0.6437	Remote Similarity	NPD6115	Approved
0.6437	Remote Similarity	NPD6118	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6421	Remote Similarity	NPD7515	Phase 2
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD4623	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD5223	Approved
0.6392	Remote Similarity	NPD5654	Approved
0.6386	Remote Similarity	NPD4245	Approved
0.6386	Remote Similarity	NPD4244	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6375	Remote Similarity	NPD7341	Phase 2
0.6374	Remote Similarity	NPD3668	Phase 3
0.6353	Remote Similarity	NPD5733	Approved
0.6353	Remote Similarity	NPD4687	Approved
0.6353	Remote Similarity	NPD4058	Approved
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.6333	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7732	Phase 3
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.631	Remote Similarity	NPD5777	Approved
0.631	Remote Similarity	NPD5276	Approved
0.6304	Remote Similarity	NPD1694	Approved
0.63	Remote Similarity	NPD4700	Approved
0.6289	Remote Similarity	NPD7748	Approved
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6279	Remote Similarity	NPD3703	Phase 2
0.6277	Remote Similarity	NPD4518	Approved
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.6263	Remote Similarity	NPD5959	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6614	Approved
0.6214	Remote Similarity	NPD5141	Approved
0.6204	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6008	Approved
0.6145	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD9298	Approved
0.6118	Remote Similarity	NPD4243	Approved
0.6117	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD6052	Approved
0.6111	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6098	Remote Similarity	NPD7331	Phase 2
0.6091	Remote Similarity	NPD6274	Approved
0.6091	Remote Similarity	NPD6868	Approved
0.6087	Remote Similarity	NPD5362	Discontinued
0.6067	Remote Similarity	NPD5364	Discontinued
0.6061	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD344	Approved
0.6056	Remote Similarity	NPD345	Approved
0.6056	Remote Similarity	NPD343	Approved
0.6044	Remote Similarity	NPD857	Phase 3
0.604	Remote Similarity	NPD7638	Approved
0.6038	Remote Similarity	NPD4729	Approved
0.6038	Remote Similarity	NPD5128	Approved
0.6038	Remote Similarity	NPD4730	Approved
0.6038	Remote Similarity	NPD5168	Approved
0.6036	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4768	Approved
0.5982	Remote Similarity	NPD6314	Approved
0.5982	Remote Similarity	NPD6313	Approved
0.5982	Remote Similarity	NPD6335	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5979	Remote Similarity	NPD5785	Approved
0.5978	Remote Similarity	NPD6435	Approved
0.5977	Remote Similarity	NPD4784	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