NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	728.21
Volume:	718.561
LogP:	4.23
LogD:	3.256
LogS:	-3.929
# Rotatable Bonds:	15
TPSA:	218.74
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.064
Synthetic Accessibility Score:	4.464
Fsp3:	0.205
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.066
MDCK Permeability:	8.09767789178295e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.722
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.39535522460938%
Volume Distribution (VD):	0.383
Pgp-substrate:	1.357815146446228%

ADMET: Metabolism

CYP1A2-inhibitor:	0.461
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.534
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	9.122
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.354
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.495
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.958
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC469343

Natural Product ID:	NPC469343
*Common Name:**	Coprinastatin 1
IUPAC Name:	(2S,3aR,4S)-2-(hydroxymethyl)-2,7-dimethyl-5-methylidenespiro[1,3,3a,4-tetrahydroindene-6,1'-cyclopropane]-4-ol
Synonyms:	Coprinastatin 1
Standard InCHIKey:	XUXXDJLUAMCRLH-MGPQQGTHSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9-11-6-14(3,8-16)7-12(11)13(17)10(2)15(9)4-5-15/h12-13,16-17H,2,4-8H2,1,3H3/t12-,13-,14-/m1/s1
SMILES:	OC[C@@]1(C)C[C@@H]2C(=C(C)C3(C(=C)[C@H]2O)CC3)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1075892
PubChem CID:	45380084
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO33262	coprinus cinereus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919060]
NPO33262	coprinus cinereus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20598551]

☑ 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
ED50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.3	ug ml-1	PMID[497193]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	32.0	ug.mL-1	PMID[497193]

☑ 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 NPC469343 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	146
0.1-0.2	1786
0.2-0.3	10078
0.3-0.4	15291
0.4-0.5	7756
0.5-0.6	6095
0.6-0.7	1405
0.7-0.8	136
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8235	Intermediate Similarity	NPC83200
0.8077	Intermediate Similarity	NPC209620
0.8077	Intermediate Similarity	NPC23852
0.8	Intermediate Similarity	NPC287339
0.8	Intermediate Similarity	NPC300442
0.7975	Intermediate Similarity	NPC50964
0.7922	Intermediate Similarity	NPC87604
0.7922	Intermediate Similarity	NPC474216
0.7917	Intermediate Similarity	NPC96484
0.7895	Intermediate Similarity	NPC253190
0.7867	Intermediate Similarity	NPC306727
0.7867	Intermediate Similarity	NPC469534
0.7867	Intermediate Similarity	NPC469533
0.7867	Intermediate Similarity	NPC469593
0.7857	Intermediate Similarity	NPC309300
0.7838	Intermediate Similarity	NPC471662
0.7838	Intermediate Similarity	NPC477792
0.7821	Intermediate Similarity	NPC109546
0.7821	Intermediate Similarity	NPC81306
0.7821	Intermediate Similarity	NPC143182
0.7821	Intermediate Similarity	NPC30986
0.7821	Intermediate Similarity	NPC84694
0.7821	Intermediate Similarity	NPC28862
0.7821	Intermediate Similarity	NPC209430
0.7821	Intermediate Similarity	NPC47982
0.7805	Intermediate Similarity	NPC94462
0.7805	Intermediate Similarity	NPC261266
0.7805	Intermediate Similarity	NPC6391
0.7792	Intermediate Similarity	NPC34019
0.7778	Intermediate Similarity	NPC82337
0.7746	Intermediate Similarity	NPC61503
0.7722	Intermediate Similarity	NPC234193
0.7722	Intermediate Similarity	NPC26117
0.7722	Intermediate Similarity	NPC241290
0.7722	Intermediate Similarity	NPC96362
0.7722	Intermediate Similarity	NPC164840
0.7722	Intermediate Similarity	NPC324772
0.7722	Intermediate Similarity	NPC209944
0.7703	Intermediate Similarity	NPC92801
0.7692	Intermediate Similarity	NPC476314
0.7692	Intermediate Similarity	NPC275910
0.7692	Intermediate Similarity	NPC473943
0.7671	Intermediate Similarity	NPC245795
0.7671	Intermediate Similarity	NPC471238
0.7671	Intermediate Similarity	NPC167527
0.7662	Intermediate Similarity	NPC321381
0.7662	Intermediate Similarity	NPC265588
0.7662	Intermediate Similarity	NPC73875
0.7662	Intermediate Similarity	NPC107059
0.7662	Intermediate Similarity	NPC321016
0.7654	Intermediate Similarity	NPC317458
0.7654	Intermediate Similarity	NPC113978
0.7654	Intermediate Similarity	NPC475789
0.7625	Intermediate Similarity	NPC470383
0.7625	Intermediate Similarity	NPC476646
0.7625	Intermediate Similarity	NPC320525
0.7625	Intermediate Similarity	NPC264245
0.7619	Intermediate Similarity	NPC474668
0.7606	Intermediate Similarity	NPC290367
0.7606	Intermediate Similarity	NPC96793
0.7606	Intermediate Similarity	NPC323424
0.7606	Intermediate Similarity	NPC219940
0.759	Intermediate Similarity	NPC152808
0.759	Intermediate Similarity	NPC293287
0.7568	Intermediate Similarity	NPC90115
0.7568	Intermediate Similarity	NPC217570
0.7564	Intermediate Similarity	NPC318495
0.7564	Intermediate Similarity	NPC198968
0.7564	Intermediate Similarity	NPC257191
0.7564	Intermediate Similarity	NPC214570
0.7564	Intermediate Similarity	NPC31037
0.7564	Intermediate Similarity	NPC155986
0.7564	Intermediate Similarity	NPC471798
0.7564	Intermediate Similarity	NPC331618
0.7561	Intermediate Similarity	NPC238485
0.7561	Intermediate Similarity	NPC474047
0.7561	Intermediate Similarity	NPC209802
0.7561	Intermediate Similarity	NPC124172
0.7534	Intermediate Similarity	NPC136813
0.7534	Intermediate Similarity	NPC114651
0.7534	Intermediate Similarity	NPC96962
0.7534	Intermediate Similarity	NPC477791
0.7532	Intermediate Similarity	NPC121744
0.7532	Intermediate Similarity	NPC230301
0.7532	Intermediate Similarity	NPC136188
0.7532	Intermediate Similarity	NPC285893
0.7532	Intermediate Similarity	NPC257347
0.7532	Intermediate Similarity	NPC288035
0.7532	Intermediate Similarity	NPC162742
0.7532	Intermediate Similarity	NPC471723
0.7532	Intermediate Similarity	NPC118508
0.7532	Intermediate Similarity	NPC141071
0.7532	Intermediate Similarity	NPC134847
0.7532	Intermediate Similarity	NPC322353
0.7532	Intermediate Similarity	NPC304309
0.7532	Intermediate Similarity	NPC28657
0.7532	Intermediate Similarity	NPC22105
0.7532	Intermediate Similarity	NPC313185
0.7531	Intermediate Similarity	NPC189972
0.7531	Intermediate Similarity	NPC202389
0.7531	Intermediate Similarity	NPC470614
0.7531	Intermediate Similarity	NPC87489
0.7531	Intermediate Similarity	NPC49964
0.7531	Intermediate Similarity	NPC1272
0.7531	Intermediate Similarity	NPC248886
0.7531	Intermediate Similarity	NPC101462
0.7529	Intermediate Similarity	NPC470361
0.75	Intermediate Similarity	NPC220939
0.75	Intermediate Similarity	NPC265485
0.75	Intermediate Similarity	NPC47149
0.75	Intermediate Similarity	NPC234527
0.75	Intermediate Similarity	NPC14352
0.75	Intermediate Similarity	NPC474140
0.747	Intermediate Similarity	NPC470360
0.7468	Intermediate Similarity	NPC472500
0.7468	Intermediate Similarity	NPC302041
0.7468	Intermediate Similarity	NPC472342
0.7468	Intermediate Similarity	NPC472499
0.7468	Intermediate Similarity	NPC65897
0.7468	Intermediate Similarity	NPC477522
0.7468	Intermediate Similarity	NPC85346
0.7467	Intermediate Similarity	NPC34834
0.7467	Intermediate Similarity	NPC254845
0.7465	Intermediate Similarity	NPC473508
0.7442	Intermediate Similarity	NPC11216
0.7442	Intermediate Similarity	NPC204188
0.7442	Intermediate Similarity	NPC3345
0.7442	Intermediate Similarity	NPC295668
0.7442	Intermediate Similarity	NPC291484
0.7442	Intermediate Similarity	NPC329596
0.7442	Intermediate Similarity	NPC80561
0.7439	Intermediate Similarity	NPC320548
0.7439	Intermediate Similarity	NPC474634
0.7439	Intermediate Similarity	NPC470384
0.7439	Intermediate Similarity	NPC82623
0.7436	Intermediate Similarity	NPC46160
0.7436	Intermediate Similarity	NPC126969
0.7436	Intermediate Similarity	NPC134330
0.7436	Intermediate Similarity	NPC470362
0.7436	Intermediate Similarity	NPC189883
0.7436	Intermediate Similarity	NPC96319
0.7436	Intermediate Similarity	NPC244488
0.7436	Intermediate Similarity	NPC129165
0.7436	Intermediate Similarity	NPC247325
0.7436	Intermediate Similarity	NPC240604
0.7436	Intermediate Similarity	NPC300324
0.7436	Intermediate Similarity	NPC113733
0.7436	Intermediate Similarity	NPC202642
0.7432	Intermediate Similarity	NPC276616
0.7432	Intermediate Similarity	NPC208999
0.7429	Intermediate Similarity	NPC135648
0.7416	Intermediate Similarity	NPC54248
0.7416	Intermediate Similarity	NPC276103
0.7412	Intermediate Similarity	NPC67872
0.7412	Intermediate Similarity	NPC133588
0.7407	Intermediate Similarity	NPC249423
0.7407	Intermediate Similarity	NPC47761
0.7407	Intermediate Similarity	NPC82986
0.7407	Intermediate Similarity	NPC474759
0.7407	Intermediate Similarity	NPC474683
0.7407	Intermediate Similarity	NPC7505
0.7407	Intermediate Similarity	NPC474731
0.7407	Intermediate Similarity	NPC474752
0.7407	Intermediate Similarity	NPC474531
0.7403	Intermediate Similarity	NPC243342
0.7403	Intermediate Similarity	NPC329090
0.7403	Intermediate Similarity	NPC472503
0.7403	Intermediate Similarity	NPC477138
0.7403	Intermediate Similarity	NPC27395
0.7403	Intermediate Similarity	NPC309178
0.7403	Intermediate Similarity	NPC471659
0.7403	Intermediate Similarity	NPC308440
0.7397	Intermediate Similarity	NPC326310
0.7397	Intermediate Similarity	NPC202017
0.7397	Intermediate Similarity	NPC267027
0.7381	Intermediate Similarity	NPC299068
0.7381	Intermediate Similarity	NPC24277
0.7381	Intermediate Similarity	NPC269058
0.7381	Intermediate Similarity	NPC255143
0.7381	Intermediate Similarity	NPC71520
0.7375	Intermediate Similarity	NPC472463
0.7375	Intermediate Similarity	NPC328714
0.7375	Intermediate Similarity	NPC24504
0.7375	Intermediate Similarity	NPC476316
0.7375	Intermediate Similarity	NPC1319
0.7368	Intermediate Similarity	NPC471272
0.7368	Intermediate Similarity	NPC164022
0.7368	Intermediate Similarity	NPC471271
0.7368	Intermediate Similarity	NPC23954
0.7368	Intermediate Similarity	NPC242001
0.7368	Intermediate Similarity	NPC471268
0.7361	Intermediate Similarity	NPC68656
0.7361	Intermediate Similarity	NPC225415
0.7361	Intermediate Similarity	NPC144650
0.7356	Intermediate Similarity	NPC97404
0.7356	Intermediate Similarity	NPC41554
0.7353	Intermediate Similarity	NPC24443
0.7349	Intermediate Similarity	NPC205845
0.7349	Intermediate Similarity	NPC185568
0.7349	Intermediate Similarity	NPC231310

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 NPC469343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	2390
0.2-0.3	4269
0.3-0.4	1719
0.4-0.5	405
0.5-0.6	170
0.6-0.7	48
0.7-0.8	8
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
0.7821	Intermediate Similarity	NPD6929	Approved
0.7722	Intermediate Similarity	NPD6930	Phase 2
0.7722	Intermediate Similarity	NPD6931	Approved
0.7625	Intermediate Similarity	NPD6902	Approved
0.7564	Intermediate Similarity	NPD5776	Phase 2
0.7564	Intermediate Similarity	NPD6925	Approved
0.7532	Intermediate Similarity	NPD6942	Approved
0.7532	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7145	Approved
0.7439	Intermediate Similarity	NPD6695	Phase 3
0.7436	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6926	Approved
0.7403	Intermediate Similarity	NPD6924	Approved
0.7349	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8264	Approved
0.7284	Intermediate Similarity	NPD7514	Phase 3
0.7262	Intermediate Similarity	NPD6893	Approved
0.7215	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD7152	Approved
0.7143	Intermediate Similarity	NPD7151	Approved
0.7143	Intermediate Similarity	NPD7150	Approved
0.7125	Intermediate Similarity	NPD6932	Approved
0.7105	Intermediate Similarity	NPD6922	Approved
0.7105	Intermediate Similarity	NPD6923	Approved
0.7093	Intermediate Similarity	NPD7750	Discontinued
0.7093	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD7525	Registered
0.7073	Intermediate Similarity	NPD4748	Discontinued
0.7073	Intermediate Similarity	NPD7332	Phase 2
0.7013	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD7143	Approved
0.6988	Remote Similarity	NPD6898	Phase 1
0.6957	Remote Similarity	NPD342	Phase 1
0.6951	Remote Similarity	NPD6683	Phase 2
0.6941	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD3667	Approved
0.6867	Remote Similarity	NPD7509	Discontinued
0.6849	Remote Similarity	NPD368	Approved
0.6829	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7087	Discontinued
0.6747	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD1696	Phase 3
0.6591	Remote Similarity	NPD3618	Phase 1
0.6556	Remote Similarity	NPD5328	Approved
0.6543	Remote Similarity	NPD4785	Approved
0.6543	Remote Similarity	NPD4784	Approved
0.65	Remote Similarity	NPD4243	Approved
0.642	Remote Similarity	NPD4732	Discontinued
0.6413	Remote Similarity	NPD7637	Suspended
0.6413	Remote Similarity	NPD6079	Approved
0.6404	Remote Similarity	NPD5279	Phase 3
0.6389	Remote Similarity	NPD4219	Approved
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3666	Approved
0.6344	Remote Similarity	NPD4202	Approved
0.6304	Remote Similarity	NPD7136	Phase 2
0.6289	Remote Similarity	NPD7639	Approved
0.6289	Remote Similarity	NPD7640	Approved
0.6265	Remote Similarity	NPD4190	Phase 3
0.6265	Remote Similarity	NPD5275	Approved
0.6235	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1346	Approved
0.6186	Remote Similarity	NPD7638	Approved
0.618	Remote Similarity	NPD3668	Phase 3
0.617	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD5779	Approved
0.617	Remote Similarity	NPD5778	Approved
0.6163	Remote Similarity	NPD4195	Approved
0.6162	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD5222	Approved
0.6146	Remote Similarity	NPD5221	Approved
0.6146	Remote Similarity	NPD4697	Phase 3
0.6146	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4755	Approved
0.6082	Remote Similarity	NPD5173	Approved
0.6067	Remote Similarity	NPD5331	Approved
0.6067	Remote Similarity	NPD5332	Approved
0.6067	Remote Similarity	NPD5362	Discontinued
0.604	Remote Similarity	NPD5141	Approved
0.6023	Remote Similarity	NPD4790	Discontinued
0.6022	Remote Similarity	NPD4753	Phase 2
0.602	Remote Similarity	NPD4225	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD4696	Approved
0.596	Remote Similarity	NPD5286	Approved
0.5955	Remote Similarity	NPD4221	Approved
0.5955	Remote Similarity	NPD4223	Phase 3
0.5909	Remote Similarity	NPD4820	Approved
0.5909	Remote Similarity	NPD4819	Approved
0.5909	Remote Similarity	NPD4822	Approved
0.5909	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD5223	Approved
0.59	Remote Similarity	NPD4159	Approved
0.59	Remote Similarity	NPD5344	Discontinued
0.5895	Remote Similarity	NPD7515	Phase 2
0.5895	Remote Similarity	NPD6411	Approved
0.5862	Remote Similarity	NPD4268	Approved
0.5862	Remote Similarity	NPD4271	Approved
0.5859	Remote Similarity	NPD5290	Discontinued
0.5842	Remote Similarity	NPD7632	Discontinued
0.5842	Remote Similarity	NPD4633	Approved
0.5842	Remote Similarity	NPD5225	Approved
0.5842	Remote Similarity	NPD5224	Approved
0.5842	Remote Similarity	NPD5226	Approved
0.5824	Remote Similarity	NPD4197	Approved
0.5789	Remote Similarity	NPD3168	Discontinued
0.5784	Remote Similarity	NPD5175	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5784	Remote Similarity	NPD5174	Approved
0.5778	Remote Similarity	NPD4270	Approved
0.5778	Remote Similarity	NPD4269	Approved
0.5761	Remote Similarity	NPD5329	Approved
0.5755	Remote Similarity	NPD4634	Approved
0.5745	Remote Similarity	NPD4518	Approved
0.573	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4695	Discontinued
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5699	Remote Similarity	NPD4694	Approved
0.5699	Remote Similarity	NPD4693	Phase 3
0.5699	Remote Similarity	NPD5280	Approved
0.5699	Remote Similarity	NPD4249	Approved
0.5699	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD5690	Phase 2
0.5699	Remote Similarity	NPD4690	Approved
0.5699	Remote Similarity	NPD4519	Discontinued
0.5699	Remote Similarity	NPD4689	Approved
0.5699	Remote Similarity	NPD4138	Approved
0.5699	Remote Similarity	NPD5205	Approved
0.5699	Remote Similarity	NPD4688	Approved
0.5684	Remote Similarity	NPD6051	Approved
0.5684	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6101	Approved
0.5682	Remote Similarity	NPD3617	Approved
0.5673	Remote Similarity	NPD7128	Approved
0.5673	Remote Similarity	NPD6402	Approved
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD6640	Phase 3
0.5673	Remote Similarity	NPD4768	Approved
0.5673	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD5739	Approved
0.5673	Remote Similarity	NPD7333	Discontinued
0.5673	Remote Similarity	NPD6008	Approved
0.5667	Remote Similarity	NPD4139	Approved
0.5667	Remote Similarity	NPD4692	Approved
0.5663	Remote Similarity	NPD15	Approved
0.5663	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD791	Approved
0.5644	Remote Similarity	NPD6648	Approved
0.5641	Remote Similarity	NPD1145	Discontinued
0.5638	Remote Similarity	NPD4250	Approved
0.5638	Remote Similarity	NPD4251	Approved
0.5625	Remote Similarity	NPD5785	Approved
0.5625	Remote Similarity	NPD7838	Discovery
0.5625	Remote Similarity	NPD6698	Approved
0.5625	Remote Similarity	NPD46	Approved
0.5625	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD7748	Approved
0.5612	Remote Similarity	NPD5282	Discontinued
0.5607	Remote Similarity	NPD6371	Approved
0.56	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD6083	Phase 2

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