NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.544
LogD:	1.938
LogS:	-3.672
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.708
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.81
MDCK Permeability:	2.7262396542937495e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	83.64710235595703%
Volume Distribution (VD):	0.877
Pgp-substrate:	28.05771827697754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.75
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.566
CYP2C9-substrate:	0.574
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.485

ADMET: Excretion

Clearance (CL):	6.371
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.676
Skin Sensitization:	0.781
Carcinogencity:	0.763
Eye Corrosion:	0.027
Eye Irritation:	0.132
Respiratory Toxicity:	0.228

Download Data

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

Natural Product: NPC47747

Natural Product ID:	NPC47747
*Common Name:**	Capillosanane Q
IUPAC Name:	(4Z,5R,10R)-2,2,10-trimethyl-4-(2-oxopropylidene)-6-oxaspiro[4.5]decan-7-one
Synonyms:
Standard InCHIKey:	IBQIHYCIZUNKBO-LZAIWYQLSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-10-5-6-13(17)18-15(10)9-14(3,4)8-12(15)7-11(2)16/h7,10H,5-6,8-9H2,1-4H3/b12-7-/t10-,15-/m1/s1
SMILES:	O=C1CC[C@H]([C@]2(O1)CC(C/C/2=C/C(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419329
PubChem CID:	73349164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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[460765]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460765]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460765]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460765]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460765]

☑ 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 NPC47747 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	186
0.1-0.2	1259
0.2-0.3	5840
0.3-0.4	14024
0.4-0.5	10131
0.5-0.6	6384
0.6-0.7	4214
0.7-0.8	644
0.8-0.85	12
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC63445
0.9211	High Similarity	NPC222210
0.8375	Intermediate Similarity	NPC469690
0.8354	Intermediate Similarity	NPC122264
0.825	Intermediate Similarity	NPC471220
0.8148	Intermediate Similarity	NPC469620
0.8148	Intermediate Similarity	NPC469617
0.8125	Intermediate Similarity	NPC53581
0.8125	Intermediate Similarity	NPC103987
0.8095	Intermediate Similarity	NPC238197
0.8068	Intermediate Similarity	NPC221282
0.8	Intermediate Similarity	NPC473223
0.7976	Intermediate Similarity	NPC193198
0.7912	Intermediate Similarity	NPC9812
0.7907	Intermediate Similarity	NPC469676
0.7907	Intermediate Similarity	NPC474045
0.7907	Intermediate Similarity	NPC261253
0.7882	Intermediate Similarity	NPC475100
0.7882	Intermediate Similarity	NPC149869
0.7865	Intermediate Similarity	NPC290651
0.7865	Intermediate Similarity	NPC472953
0.7826	Intermediate Similarity	NPC69385
0.7826	Intermediate Similarity	NPC47834
0.7791	Intermediate Similarity	NPC161957
0.7791	Intermediate Similarity	NPC189311
0.7766	Intermediate Similarity	NPC475099
0.7766	Intermediate Similarity	NPC206079
0.7765	Intermediate Similarity	NPC53867
0.7742	Intermediate Similarity	NPC244411
0.7742	Intermediate Similarity	NPC222011
0.7742	Intermediate Similarity	NPC64742
0.7711	Intermediate Similarity	NPC150646
0.7701	Intermediate Similarity	NPC220478
0.7692	Intermediate Similarity	NPC265574
0.7667	Intermediate Similarity	NPC45579
0.766	Intermediate Similarity	NPC280963
0.7654	Intermediate Similarity	NPC244166
0.7647	Intermediate Similarity	NPC186276
0.7647	Intermediate Similarity	NPC200513
0.764	Intermediate Similarity	NPC285982
0.7625	Intermediate Similarity	NPC135703
0.7614	Intermediate Similarity	NPC231599
0.759	Intermediate Similarity	NPC128276
0.759	Intermediate Similarity	NPC474341
0.7586	Intermediate Similarity	NPC177932
0.7586	Intermediate Similarity	NPC110405
0.7586	Intermediate Similarity	NPC245434
0.7579	Intermediate Similarity	NPC477950
0.7579	Intermediate Similarity	NPC62670
0.7579	Intermediate Similarity	NPC116139
0.7561	Intermediate Similarity	NPC40353
0.7561	Intermediate Similarity	NPC226242
0.7561	Intermediate Similarity	NPC27205
0.7558	Intermediate Similarity	NPC22611
0.7558	Intermediate Similarity	NPC39588
0.7558	Intermediate Similarity	NPC65350
0.7556	Intermediate Similarity	NPC77337
0.7556	Intermediate Similarity	NPC152467
0.7553	Intermediate Similarity	NPC176845
0.7531	Intermediate Similarity	NPC167049
0.7531	Intermediate Similarity	NPC469691
0.7529	Intermediate Similarity	NPC282293
0.75	Intermediate Similarity	NPC472863
0.75	Intermediate Similarity	NPC66110
0.75	Intermediate Similarity	NPC148463
0.75	Intermediate Similarity	NPC234038
0.7473	Intermediate Similarity	NPC284185
0.7473	Intermediate Similarity	NPC218301
0.7473	Intermediate Similarity	NPC472705
0.7471	Intermediate Similarity	NPC196487
0.7471	Intermediate Similarity	NPC474359
0.7471	Intermediate Similarity	NPC30486
0.7471	Intermediate Similarity	NPC14575
0.747	Intermediate Similarity	NPC316500
0.747	Intermediate Similarity	NPC41780
0.747	Intermediate Similarity	NPC187568
0.747	Intermediate Similarity	NPC65603
0.747	Intermediate Similarity	NPC57744
0.747	Intermediate Similarity	NPC316324
0.747	Intermediate Similarity	NPC54996
0.747	Intermediate Similarity	NPC180290
0.7447	Intermediate Similarity	NPC477949
0.7444	Intermediate Similarity	NPC284561
0.7444	Intermediate Similarity	NPC173042
0.7444	Intermediate Similarity	NPC5509
0.7444	Intermediate Similarity	NPC305039
0.7442	Intermediate Similarity	NPC475936
0.7439	Intermediate Similarity	NPC469678
0.7439	Intermediate Similarity	NPC469669
0.7439	Intermediate Similarity	NPC475771
0.7423	Intermediate Similarity	NPC470954
0.7419	Intermediate Similarity	NPC473369
0.7419	Intermediate Similarity	NPC470974
0.7419	Intermediate Similarity	NPC171395
0.7419	Intermediate Similarity	NPC470978
0.7416	Intermediate Similarity	NPC478145
0.7416	Intermediate Similarity	NPC30421
0.7416	Intermediate Similarity	NPC312561
0.7412	Intermediate Similarity	NPC290508
0.7412	Intermediate Similarity	NPC195424
0.7412	Intermediate Similarity	NPC73052
0.7412	Intermediate Similarity	NPC293418
0.7412	Intermediate Similarity	NPC233377
0.7407	Intermediate Similarity	NPC300940
0.7407	Intermediate Similarity	NPC92909
0.7407	Intermediate Similarity	NPC107783
0.7396	Intermediate Similarity	NPC310981
0.7391	Intermediate Similarity	NPC109414
0.7386	Intermediate Similarity	NPC86316
0.7386	Intermediate Similarity	NPC33570
0.7386	Intermediate Similarity	NPC106416
0.7386	Intermediate Similarity	NPC323765
0.7386	Intermediate Similarity	NPC474547
0.7386	Intermediate Similarity	NPC21471
0.7386	Intermediate Similarity	NPC65661
0.7381	Intermediate Similarity	NPC184737
0.7381	Intermediate Similarity	NPC474056
0.7381	Intermediate Similarity	NPC299235
0.7363	Intermediate Similarity	NPC49946
0.7363	Intermediate Similarity	NPC471818
0.7363	Intermediate Similarity	NPC306168
0.7363	Intermediate Similarity	NPC51486
0.7363	Intermediate Similarity	NPC62815
0.7363	Intermediate Similarity	NPC476437
0.7363	Intermediate Similarity	NPC253144
0.7363	Intermediate Similarity	NPC476369
0.7363	Intermediate Similarity	NPC8062
0.7356	Intermediate Similarity	NPC222358
0.7356	Intermediate Similarity	NPC108045
0.7356	Intermediate Similarity	NPC475622
0.7349	Intermediate Similarity	NPC476317
0.7349	Intermediate Similarity	NPC235906
0.7347	Intermediate Similarity	NPC169843
0.7347	Intermediate Similarity	NPC309190
0.734	Intermediate Similarity	NPC29952
0.7333	Intermediate Similarity	NPC472302
0.7333	Intermediate Similarity	NPC215831
0.7333	Intermediate Similarity	NPC226863
0.7333	Intermediate Similarity	NPC469631
0.7333	Intermediate Similarity	NPC471047
0.7333	Intermediate Similarity	NPC469653
0.7333	Intermediate Similarity	NPC475906
0.7333	Intermediate Similarity	NPC469628
0.7326	Intermediate Similarity	NPC475665
0.7326	Intermediate Similarity	NPC477372
0.7326	Intermediate Similarity	NPC325031
0.7326	Intermediate Similarity	NPC471325
0.7326	Intermediate Similarity	NPC40228
0.7326	Intermediate Similarity	NPC42470
0.7326	Intermediate Similarity	NPC10276
0.7326	Intermediate Similarity	NPC35089
0.7317	Intermediate Similarity	NPC20025
0.7317	Intermediate Similarity	NPC206875
0.7312	Intermediate Similarity	NPC53685
0.7312	Intermediate Similarity	NPC475572
0.7312	Intermediate Similarity	NPC90453
0.7312	Intermediate Similarity	NPC476415
0.7308	Intermediate Similarity	NPC116013
0.7303	Intermediate Similarity	NPC195640
0.7303	Intermediate Similarity	NPC198314
0.7294	Intermediate Similarity	NPC182550
0.7294	Intermediate Similarity	NPC471890
0.7294	Intermediate Similarity	NPC66677
0.7294	Intermediate Similarity	NPC84185
0.7294	Intermediate Similarity	NPC471299
0.7294	Intermediate Similarity	NPC178277
0.7284	Intermediate Similarity	NPC469737
0.7284	Intermediate Similarity	NPC129665
0.7283	Intermediate Similarity	NPC150978
0.7283	Intermediate Similarity	NPC300312
0.7283	Intermediate Similarity	NPC478243
0.7283	Intermediate Similarity	NPC74103
0.7283	Intermediate Similarity	NPC111114
0.7283	Intermediate Similarity	NPC219874
0.7283	Intermediate Similarity	NPC70595
0.7283	Intermediate Similarity	NPC261607
0.7283	Intermediate Similarity	NPC478244
0.7283	Intermediate Similarity	NPC123177
0.7273	Intermediate Similarity	NPC9868
0.7273	Intermediate Similarity	NPC243618
0.7273	Intermediate Similarity	NPC70424
0.7273	Intermediate Similarity	NPC72464
0.7263	Intermediate Similarity	NPC474343
0.7263	Intermediate Similarity	NPC84335
0.7263	Intermediate Similarity	NPC38530
0.7262	Intermediate Similarity	NPC189206
0.7262	Intermediate Similarity	NPC97377
0.7262	Intermediate Similarity	NPC107668
0.7262	Intermediate Similarity	NPC472300
0.7253	Intermediate Similarity	NPC474679
0.7253	Intermediate Similarity	NPC288699
0.7253	Intermediate Similarity	NPC212598
0.7253	Intermediate Similarity	NPC115179
0.7253	Intermediate Similarity	NPC106040
0.7253	Intermediate Similarity	NPC232747
0.7253	Intermediate Similarity	NPC73995
0.7241	Intermediate Similarity	NPC178676
0.7241	Intermediate Similarity	NPC35556
0.7241	Intermediate Similarity	NPC221231
0.7241	Intermediate Similarity	NPC471326

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 NPC47747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1566
0.2-0.3	4172
0.3-0.4	2166
0.4-0.5	650
0.5-0.6	237
0.6-0.7	152
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7865	Intermediate Similarity	NPD5693	Phase 1
0.7647	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1694	Approved
0.7528	Intermediate Similarity	NPD5208	Approved
0.7444	Intermediate Similarity	NPD6080	Approved
0.7444	Intermediate Similarity	NPD6904	Approved
0.7444	Intermediate Similarity	NPD6673	Approved
0.7416	Intermediate Similarity	NPD3573	Approved
0.7363	Intermediate Similarity	NPD5207	Approved
0.7363	Intermediate Similarity	NPD5692	Phase 3
0.7303	Intermediate Similarity	NPD6409	Approved
0.7303	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD7334	Approved
0.7303	Intermediate Similarity	NPD6098	Approved
0.7303	Intermediate Similarity	NPD6684	Approved
0.7303	Intermediate Similarity	NPD7146	Approved
0.7303	Intermediate Similarity	NPD5330	Approved
0.7283	Intermediate Similarity	NPD5694	Approved
0.7283	Intermediate Similarity	NPD6050	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6672	Approved
0.7128	Intermediate Similarity	NPD6001	Approved
0.7053	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5695	Phase 3
0.7045	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD4221	Approved
0.7024	Intermediate Similarity	NPD8039	Approved
0.6989	Remote Similarity	NPD5785	Approved
0.6915	Remote Similarity	NPD5281	Approved
0.6915	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD6083	Phase 2
0.6907	Remote Similarity	NPD6084	Phase 2
0.6889	Remote Similarity	NPD4197	Approved
0.6882	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD7331	Phase 2
0.6875	Remote Similarity	NPD5654	Approved
0.6854	Remote Similarity	NPD5209	Approved
0.6837	Remote Similarity	NPD5696	Approved
0.6813	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5329	Approved
0.6782	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5739	Approved
0.6765	Remote Similarity	NPD6675	Approved
0.6765	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD6008	Approved
0.6765	Remote Similarity	NPD7128	Approved
0.675	Remote Similarity	NPD7341	Phase 2
0.675	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4694	Approved
0.6739	Remote Similarity	NPD4138	Approved
0.6739	Remote Similarity	NPD4693	Phase 3
0.6739	Remote Similarity	NPD5690	Phase 2
0.6739	Remote Similarity	NPD4688	Approved
0.6739	Remote Similarity	NPD4689	Approved
0.6739	Remote Similarity	NPD5280	Approved
0.6739	Remote Similarity	NPD5205	Approved
0.6739	Remote Similarity	NPD4690	Approved
0.6735	Remote Similarity	NPD5959	Approved
0.6702	Remote Similarity	NPD6051	Approved
0.6699	Remote Similarity	NPD5697	Approved
0.6699	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6635	Remote Similarity	NPD6899	Approved
0.6635	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD7320	Approved
0.66	Remote Similarity	NPD7639	Approved
0.66	Remote Similarity	NPD7640	Approved
0.6596	Remote Similarity	NPD4518	Approved
0.6593	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD6013	Approved
0.6571	Remote Similarity	NPD6372	Approved
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6571	Remote Similarity	NPD6373	Approved
0.6569	Remote Similarity	NPD6052	Approved
0.6559	Remote Similarity	NPD5786	Approved
0.6559	Remote Similarity	NPD4623	Approved
0.6559	Remote Similarity	NPD4519	Discontinued
0.6548	Remote Similarity	NPD4747	Approved
0.6542	Remote Similarity	NPD6053	Discontinued
0.6526	Remote Similarity	NPD5328	Approved
0.6526	Remote Similarity	NPD4753	Phase 2
0.6522	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD3666	Approved
0.6522	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD6371	Approved
0.6509	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD6883	Approved
0.6509	Remote Similarity	NPD7102	Approved
0.6495	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD5276	Approved
0.6458	Remote Similarity	NPD46	Approved
0.6458	Remote Similarity	NPD4096	Approved
0.6458	Remote Similarity	NPD6698	Approved
0.6452	Remote Similarity	NPD5363	Approved
0.6452	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD6869	Approved
0.6449	Remote Similarity	NPD6617	Approved
0.6449	Remote Similarity	NPD6650	Approved
0.6449	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6847	Approved
0.6444	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD4137	Phase 3
0.64	Remote Similarity	NPD4755	Approved
0.6392	Remote Similarity	NPD6411	Approved
0.6392	Remote Similarity	NPD6079	Approved
0.6389	Remote Similarity	NPD8297	Approved
0.6389	Remote Similarity	NPD6882	Approved
0.6383	Remote Similarity	NPD5279	Phase 3
0.6381	Remote Similarity	NPD6614	Approved
0.6374	Remote Similarity	NPD5369	Approved
0.6353	Remote Similarity	NPD4691	Approved
0.6333	Remote Similarity	NPD4195	Approved
0.6327	Remote Similarity	NPD4202	Approved
0.6322	Remote Similarity	NPD4687	Approved
0.6322	Remote Similarity	NPD5733	Approved
0.6321	Remote Similarity	NPD6686	Approved
0.6311	Remote Similarity	NPD5211	Phase 2
0.6306	Remote Similarity	NPD7115	Discovery
0.6304	Remote Similarity	NPD4269	Approved
0.6304	Remote Similarity	NPD4270	Approved
0.6304	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7507	Approved
0.6275	Remote Similarity	NPD5286	Approved
0.6275	Remote Similarity	NPD5285	Approved
0.6275	Remote Similarity	NPD4700	Approved
0.6275	Remote Similarity	NPD4696	Approved
0.6264	Remote Similarity	NPD4695	Discontinued
0.6263	Remote Similarity	NPD5282	Discontinued
0.6263	Remote Similarity	NPD7900	Approved
0.6263	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7748	Approved
0.6237	Remote Similarity	NPD7154	Phase 3
0.6222	Remote Similarity	NPD3617	Approved
0.6216	Remote Similarity	NPD6274	Approved
0.6214	Remote Similarity	NPD5223	Approved
0.6211	Remote Similarity	NPD3618	Phase 1
0.6211	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4629	Approved
0.62	Remote Similarity	NPD5210	Approved
0.6196	Remote Similarity	NPD4139	Approved
0.6196	Remote Similarity	NPD857	Phase 3
0.6196	Remote Similarity	NPD4692	Approved
0.619	Remote Similarity	NPD5141	Approved
0.6186	Remote Similarity	NPD6101	Approved
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4632	Approved
0.6176	Remote Similarity	NPD4225	Approved
0.617	Remote Similarity	NPD4786	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5133	Approved
0.6161	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6139	Remote Similarity	NPD5222	Approved
0.6139	Remote Similarity	NPD5221	Approved
0.6139	Remote Similarity	NPD4697	Phase 3
0.6139	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4058	Approved
0.6134	Remote Similarity	NPD7319	Approved
0.6129	Remote Similarity	NPD3667	Approved
0.6117	Remote Similarity	NPD6404	Discontinued
0.6106	Remote Similarity	NPD6314	Approved
0.6106	Remote Similarity	NPD6335	Approved
0.6106	Remote Similarity	NPD6313	Approved
0.6095	Remote Similarity	NPD5174	Approved
0.6095	Remote Similarity	NPD5175	Approved
0.6095	Remote Similarity	NPD4754	Approved
0.6087	Remote Similarity	NPD4252	Approved
0.6087	Remote Similarity	NPD4820	Approved
0.6087	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4822	Approved
0.6087	Remote Similarity	NPD4821	Approved
0.6087	Remote Similarity	NPD4819	Approved
0.6078	Remote Similarity	NPD5173	Approved
0.6078	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3702	Approved
0.6064	Remote Similarity	NPD5331	Approved
0.6064	Remote Similarity	NPD5332	Approved
0.6064	Remote Similarity	NPD4788	Approved
0.6061	Remote Similarity	NPD7515	Phase 2
0.6053	Remote Similarity	NPD7101	Approved
0.6053	Remote Similarity	NPD7100	Approved
0.6024	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4790	Discontinued
0.602	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD6319	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