NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	3.02
LogD:	3.015
LogS:	-3.98
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	4.117
Fsp3:	0.667
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:	-4.627
MDCK Permeability:	2.1812096747453324e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.083
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	85.64972686767578%
Volume Distribution (VD):	1.704
Pgp-substrate:	25.17656898498535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.189
CYP1A2-substrate:	0.524
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.579
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	7.449
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.239
Carcinogencity:	0.852
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.613

Download Data

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

Natural Product: NPC86917

Natural Product ID:	NPC86917
*Common Name:**	Capillosanane D
IUPAC Name:	(4Z,6S,9R)-6-hydroxy-2,2,5,9-tetramethyl-6,7,8,9-tetrahydro-1H-cyclopenta[8]annulen-3-one
Synonyms:
Standard InCHIKey:	XWJRORQTJORDHX-QBLALBGASA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9-5-6-13(16)10(2)7-11-12(9)8-15(3,4)14(11)17/h7,9,13,16H,5-6,8H2,1-4H3/b10-7-/t9-,13+/m1/s1
SMILES:	CC1=CC2=C(CC(C2=O)(C)C)[C@@H](CC[C@@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419334
PubChem CID:	73347659
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
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087604]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155971]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964704]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	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	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[573850]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[573850]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[573850]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[573850]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[573850]

☑ 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 NPC86917 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	176
0.1-0.2	1067
0.2-0.3	5976
0.3-0.4	15733
0.4-0.5	10909
0.5-0.6	6145
0.6-0.7	2367
0.7-0.8	296
0.8-0.85	22
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC474011
0.8451	Intermediate Similarity	NPC474304
0.8451	Intermediate Similarity	NPC474329
0.8312	Intermediate Similarity	NPC469646
0.8243	Intermediate Similarity	NPC90115
0.8243	Intermediate Similarity	NPC217570
0.8101	Intermediate Similarity	NPC475994
0.8072	Intermediate Similarity	NPC474853
0.8072	Intermediate Similarity	NPC179006
0.8052	Intermediate Similarity	NPC206875
0.8	Intermediate Similarity	NPC308038
0.7952	Intermediate Similarity	NPC230527
0.7952	Intermediate Similarity	NPC7927
0.7922	Intermediate Similarity	NPC275098
0.7922	Intermediate Similarity	NPC186042
0.7917	Intermediate Similarity	NPC167256
0.7907	Intermediate Similarity	NPC476388
0.7907	Intermediate Similarity	NPC477215
0.7882	Intermediate Similarity	NPC287079
0.7875	Intermediate Similarity	NPC192006
0.7867	Intermediate Similarity	NPC469679
0.7857	Intermediate Similarity	NPC15807
0.7848	Intermediate Similarity	NPC263582
0.7841	Intermediate Similarity	NPC37816
0.7821	Intermediate Similarity	NPC227396
0.7805	Intermediate Similarity	NPC470298
0.7791	Intermediate Similarity	NPC474854
0.7778	Intermediate Similarity	NPC260573
0.7778	Intermediate Similarity	NPC281138
0.7765	Intermediate Similarity	NPC194417
0.7763	Intermediate Similarity	NPC10758
0.7763	Intermediate Similarity	NPC250928
0.775	Intermediate Similarity	NPC74995
0.775	Intermediate Similarity	NPC276769
0.7733	Intermediate Similarity	NPC278895
0.7722	Intermediate Similarity	NPC114236
0.7711	Intermediate Similarity	NPC20262
0.7711	Intermediate Similarity	NPC93590
0.7711	Intermediate Similarity	NPC256750
0.7701	Intermediate Similarity	NPC170775
0.7683	Intermediate Similarity	NPC45495
0.7683	Intermediate Similarity	NPC172013
0.7654	Intermediate Similarity	NPC62336
0.7654	Intermediate Similarity	NPC169095
0.7632	Intermediate Similarity	NPC469688
0.7595	Intermediate Similarity	NPC215050
0.759	Intermediate Similarity	NPC6663
0.7586	Intermediate Similarity	NPC477710
0.7564	Intermediate Similarity	NPC288667
0.7561	Intermediate Similarity	NPC258231
0.7561	Intermediate Similarity	NPC261125
0.7561	Intermediate Similarity	NPC19900
0.7561	Intermediate Similarity	NPC152061
0.7561	Intermediate Similarity	NPC7232
0.7561	Intermediate Similarity	NPC301769
0.7561	Intermediate Similarity	NPC181195
0.7558	Intermediate Similarity	NPC476043
0.7532	Intermediate Similarity	NPC469677
0.7532	Intermediate Similarity	NPC236208
0.7532	Intermediate Similarity	NPC67608
0.7531	Intermediate Similarity	NPC211279
0.7531	Intermediate Similarity	NPC471061
0.7531	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC133844
0.75	Intermediate Similarity	NPC474885
0.75	Intermediate Similarity	NPC469678
0.75	Intermediate Similarity	NPC473999
0.75	Intermediate Similarity	NPC216791
0.75	Intermediate Similarity	NPC123912
0.75	Intermediate Similarity	NPC158411
0.75	Intermediate Similarity	NPC23231
0.75	Intermediate Similarity	NPC269985
0.75	Intermediate Similarity	NPC307092
0.75	Intermediate Similarity	NPC38796
0.75	Intermediate Similarity	NPC309603
0.75	Intermediate Similarity	NPC475771
0.75	Intermediate Similarity	NPC232747
0.75	Intermediate Similarity	NPC60818
0.75	Intermediate Similarity	NPC469669
0.7471	Intermediate Similarity	NPC136548
0.747	Intermediate Similarity	NPC157895
0.747	Intermediate Similarity	NPC104120
0.747	Intermediate Similarity	NPC148685
0.7442	Intermediate Similarity	NPC476426
0.7442	Intermediate Similarity	NPC471224
0.7442	Intermediate Similarity	NPC474083
0.7439	Intermediate Similarity	NPC321180
0.7439	Intermediate Similarity	NPC297996
0.7419	Intermediate Similarity	NPC471717
0.7416	Intermediate Similarity	NPC69622
0.7416	Intermediate Similarity	NPC48010
0.7416	Intermediate Similarity	NPC477711
0.7412	Intermediate Similarity	NPC65350
0.7407	Intermediate Similarity	NPC215481
0.7407	Intermediate Similarity	NPC279537
0.7407	Intermediate Similarity	NPC470525
0.7407	Intermediate Similarity	NPC250621
0.7386	Intermediate Similarity	NPC473658
0.7381	Intermediate Similarity	NPC136150
0.7381	Intermediate Similarity	NPC121984
0.7381	Intermediate Similarity	NPC101012
0.7375	Intermediate Similarity	NPC144995
0.7375	Intermediate Similarity	NPC227814
0.7375	Intermediate Similarity	NPC7382
0.7368	Intermediate Similarity	NPC142423
0.7368	Intermediate Similarity	NPC308294
0.7363	Intermediate Similarity	NPC53685
0.7363	Intermediate Similarity	NPC474690
0.7363	Intermediate Similarity	NPC299100
0.7363	Intermediate Similarity	NPC473162
0.7356	Intermediate Similarity	NPC472974
0.7356	Intermediate Similarity	NPC472986
0.7356	Intermediate Similarity	NPC472985
0.7349	Intermediate Similarity	NPC229204
0.7349	Intermediate Similarity	NPC32758
0.7342	Intermediate Similarity	NPC319163
0.7342	Intermediate Similarity	NPC67076
0.7342	Intermediate Similarity	NPC95863
0.7342	Intermediate Similarity	NPC29328
0.7342	Intermediate Similarity	NPC474884
0.7333	Intermediate Similarity	NPC110241
0.7333	Intermediate Similarity	NPC475806
0.7333	Intermediate Similarity	NPC473998
0.7333	Intermediate Similarity	NPC150162
0.7326	Intermediate Similarity	NPC85774
0.7326	Intermediate Similarity	NPC472326
0.7326	Intermediate Similarity	NPC476412
0.7326	Intermediate Similarity	NPC214043
0.7326	Intermediate Similarity	NPC473246
0.7326	Intermediate Similarity	NPC82297
0.7317	Intermediate Similarity	NPC476007
0.7317	Intermediate Similarity	NPC203403
0.7308	Intermediate Similarity	NPC143396
0.7303	Intermediate Similarity	NPC214387
0.7303	Intermediate Similarity	NPC51358
0.7294	Intermediate Similarity	NPC145963
0.7294	Intermediate Similarity	NPC279186
0.7284	Intermediate Similarity	NPC263698
0.7284	Intermediate Similarity	NPC251435
0.7284	Intermediate Similarity	NPC77501
0.7284	Intermediate Similarity	NPC89374
0.7283	Intermediate Similarity	NPC180950
0.7273	Intermediate Similarity	NPC141292
0.7273	Intermediate Similarity	NPC106613
0.7273	Intermediate Similarity	NPC477791
0.7273	Intermediate Similarity	NPC312561
0.7273	Intermediate Similarity	NPC237540
0.7262	Intermediate Similarity	NPC472478
0.7262	Intermediate Similarity	NPC470946
0.7262	Intermediate Similarity	NPC271104
0.7262	Intermediate Similarity	NPC471514
0.7262	Intermediate Similarity	NPC470947
0.7262	Intermediate Similarity	NPC470945
0.7262	Intermediate Similarity	NPC306095
0.7253	Intermediate Similarity	NPC472942
0.7253	Intermediate Similarity	NPC474736
0.7253	Intermediate Similarity	NPC472930
0.7253	Intermediate Similarity	NPC69454
0.7253	Intermediate Similarity	NPC134826
0.725	Intermediate Similarity	NPC323437
0.725	Intermediate Similarity	NPC29542
0.725	Intermediate Similarity	NPC247586
0.725	Intermediate Similarity	NPC201562
0.7241	Intermediate Similarity	NPC32037
0.7241	Intermediate Similarity	NPC36350
0.7237	Intermediate Similarity	NPC19569
0.7234	Intermediate Similarity	NPC103051
0.7234	Intermediate Similarity	NPC235464
0.7234	Intermediate Similarity	NPC166745
0.7229	Intermediate Similarity	NPC478122
0.7229	Intermediate Similarity	NPC231739
0.7229	Intermediate Similarity	NPC178852
0.7222	Intermediate Similarity	NPC477147
0.7222	Intermediate Similarity	NPC477149
0.7215	Intermediate Similarity	NPC286154
0.7215	Intermediate Similarity	NPC280256
0.7215	Intermediate Similarity	NPC318766
0.7215	Intermediate Similarity	NPC173321
0.7209	Intermediate Similarity	NPC251475
0.7209	Intermediate Similarity	NPC470165
0.7209	Intermediate Similarity	NPC105173
0.7209	Intermediate Similarity	NPC169941
0.7204	Intermediate Similarity	NPC301534
0.7204	Intermediate Similarity	NPC117133
0.7204	Intermediate Similarity	NPC250757
0.7195	Intermediate Similarity	NPC271070
0.7195	Intermediate Similarity	NPC182848
0.7191	Intermediate Similarity	NPC26078
0.7191	Intermediate Similarity	NPC310752
0.7191	Intermediate Similarity	NPC292491
0.7179	Intermediate Similarity	NPC167527
0.7179	Intermediate Similarity	NPC476614
0.7179	Intermediate Similarity	NPC45264
0.7179	Intermediate Similarity	NPC117804
0.7176	Intermediate Similarity	NPC4166
0.7176	Intermediate Similarity	NPC470241
0.7174	Intermediate Similarity	NPC8993
0.716	Intermediate Similarity	NPC469691
0.716	Intermediate Similarity	NPC167049
0.716	Intermediate Similarity	NPC213223

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 NPC86917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1636
0.2-0.3	4017
0.3-0.4	2339
0.4-0.5	646
0.5-0.6	272
0.6-0.7	75
0.7-0.8	5
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
0.7654	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5279	Phase 3
0.7241	Intermediate Similarity	NPD1696	Phase 3
0.7209	Intermediate Similarity	NPD5362	Discontinued
0.7126	Intermediate Similarity	NPD3665	Phase 1
0.7126	Intermediate Similarity	NPD3666	Approved
0.7126	Intermediate Similarity	NPD3133	Approved
0.7045	Intermediate Similarity	NPD5363	Approved
0.7033	Intermediate Similarity	NPD5785	Approved
0.7011	Intermediate Similarity	NPD7154	Phase 3
0.6966	Remote Similarity	NPD3618	Phase 1
0.6966	Remote Similarity	NPD4623	Approved
0.6966	Remote Similarity	NPD4519	Discontinued
0.6932	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD7331	Phase 2
0.6923	Remote Similarity	NPD5328	Approved
0.6897	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD4270	Approved
0.6897	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5280	Approved
0.6778	Remote Similarity	NPD4694	Approved
0.6774	Remote Similarity	NPD6079	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6737	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5209	Approved
0.6705	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6702	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD4518	Approved
0.6629	Remote Similarity	NPD5331	Approved
0.6629	Remote Similarity	NPD5332	Approved
0.6593	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD4790	Discontinued
0.6582	Remote Similarity	NPD7341	Phase 2
0.6556	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD6929	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6512	Remote Similarity	NPD6925	Approved
0.6512	Remote Similarity	NPD5776	Phase 2
0.6512	Remote Similarity	NPD4756	Discovery
0.6506	Remote Similarity	NPD5276	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.6495	Remote Similarity	NPD5222	Approved
0.6495	Remote Similarity	NPD5221	Approved
0.6495	Remote Similarity	NPD4697	Phase 3
0.6495	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4096	Approved
0.6484	Remote Similarity	NPD1694	Approved
0.6484	Remote Similarity	NPD5329	Approved
0.6477	Remote Similarity	NPD7514	Phase 3
0.6477	Remote Similarity	NPD6930	Phase 2
0.6477	Remote Similarity	NPD4821	Approved
0.6477	Remote Similarity	NPD6931	Approved
0.6477	Remote Similarity	NPD4819	Approved
0.6477	Remote Similarity	NPD4820	Approved
0.6477	Remote Similarity	NPD4695	Discontinued
0.6477	Remote Similarity	NPD4822	Approved
0.6477	Remote Similarity	NPD5368	Approved
0.6471	Remote Similarity	NPD8039	Approved
0.6471	Remote Similarity	NPD8264	Approved
0.6463	Remote Similarity	NPD6922	Approved
0.6463	Remote Similarity	NPD6923	Approved
0.6458	Remote Similarity	NPD5282	Discontinued
0.6437	Remote Similarity	NPD7145	Approved
0.6437	Remote Similarity	NPD4271	Approved
0.6437	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD5173	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6421	Remote Similarity	NPD7983	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD7515	Phase 2
0.6421	Remote Similarity	NPD5281	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4688	Approved
0.641	Remote Similarity	NPD368	Approved
0.6404	Remote Similarity	NPD6898	Phase 1
0.6404	Remote Similarity	NPD5369	Approved
0.6404	Remote Similarity	NPD6902	Approved
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6386	Remote Similarity	NPD7144	Approved
0.6386	Remote Similarity	NPD7143	Approved
0.6381	Remote Similarity	NPD6371	Approved
0.6373	Remote Similarity	NPD5141	Approved
0.6354	Remote Similarity	NPD5778	Approved
0.6354	Remote Similarity	NPD5779	Approved
0.6353	Remote Similarity	NPD4687	Approved
0.6353	Remote Similarity	NPD5733	Approved
0.6333	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD6698	Approved
0.631	Remote Similarity	NPD7150	Approved
0.631	Remote Similarity	NPD7152	Approved
0.631	Remote Similarity	NPD7151	Approved
0.63	Remote Similarity	NPD5286	Approved
0.63	Remote Similarity	NPD5285	Approved
0.63	Remote Similarity	NPD4700	Approved
0.63	Remote Similarity	NPD4696	Approved
0.6292	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7509	Discontinued
0.6267	Remote Similarity	NPD342	Phase 1
0.6264	Remote Similarity	NPD6695	Phase 3
0.6264	Remote Similarity	NPD4788	Approved
0.6263	Remote Similarity	NPD6084	Phase 2
0.6263	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD3617	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD857	Phase 3
0.6203	Remote Similarity	NPD4192	Approved
0.6203	Remote Similarity	NPD4194	Approved
0.6203	Remote Similarity	NPD4193	Approved
0.6203	Remote Similarity	NPD4191	Approved
0.6196	Remote Similarity	NPD3668	Phase 3
0.6196	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4747	Approved
0.6186	Remote Similarity	NPD5133	Approved
0.6186	Remote Similarity	NPD6399	Phase 3
0.6184	Remote Similarity	NPD4219	Approved
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5226	Approved
0.6163	Remote Similarity	NPD4058	Approved
0.6162	Remote Similarity	NPD7839	Suspended
0.6139	Remote Similarity	NPD7640	Approved
0.6139	Remote Similarity	NPD7639	Approved
0.6139	Remote Similarity	NPD6404	Discontinued
0.6136	Remote Similarity	NPD6932	Approved
0.6129	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6893	Approved
0.6125	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7748	Approved
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.6117	Remote Similarity	NPD6647	Phase 2
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6098	Remote Similarity	NPD3704	Approved
0.6087	Remote Similarity	NPD6110	Phase 1
0.6071	Remote Similarity	NPD4137	Phase 3
0.6064	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3197	Phase 1
0.6047	Remote Similarity	NPD4732	Discontinued
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6101	Approved
0.6042	Remote Similarity	NPD5370	Suspended
0.604	Remote Similarity	NPD5696	Approved
0.604	Remote Similarity	NPD7638	Approved
0.604	Remote Similarity	NPD4225	Approved
0.6024	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD7333	Discontinued
0.6	Remote Similarity	NPD6402	Approved
0.5979	Remote Similarity	NPD5207	Approved
0.5979	Remote Similarity	NPD5692	Phase 3
0.5979	Remote Similarity	NPD7838	Discovery
0.5976	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5701	Approved
0.5943	Remote Similarity	NPD5697	Approved
0.5941	Remote Similarity	NPD7902	Approved
0.5918	Remote Similarity	NPD5694	Approved
0.5918	Remote Similarity	NPD4810	Clinical (unspecified phase)

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