NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	286.641
LogP:	3.319
LogD:	3.043
LogS:	-4.047
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	4.413
Fsp3:	0.688
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:	-4.573
MDCK Permeability:	3.628050399129279e-05
Pgp-inhibitor:	0.364
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.741
20% Bioavailability (F20%):	0.226
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	89.0926513671875%
Volume Distribution (VD):	1.125
Pgp-substrate:	10.585735321044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.314
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	5.794
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.625
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.619
Carcinogencity:	0.063
Eye Corrosion:	0.123
Eye Irritation:	0.251
Respiratory Toxicity:	0.697

Download Data

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

Natural Product: NPC474760

Natural Product ID:	NPC474760
*Common Name:**	KYCSEGOZBNEMHU-PPHZONQLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KYCSEGOZBNEMHU-PPHZONQLSA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-11-5-4-6-12(2)9-15-13(8-7-11)14(10-18-3)16(17)19-15/h5,9,13-15H,4,6-8,10H2,1-3H3/b11-5+,12-9+/t13-,14-,15+/m0/s1
SMILES:	COC[C@@H]1C(=O)O[C@H]2[C@H]1CC/C(=C/CC/C(=C/2)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481699
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[18409040]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[18579374]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25068579]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[8541643]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	220.0	ug.mL-1	PMID[496071]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	75.05	ug.mL-1	PMID[496071]

☑ 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 NPC474760 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	191
0.1-0.2	1319
0.2-0.3	6319
0.3-0.4	16038
0.4-0.5	9259
0.5-0.6	6564
0.6-0.7	2399
0.7-0.8	507
0.8-0.85	74
0.85-0.9	25
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC129665
0.8933	High Similarity	NPC141789
0.8933	High Similarity	NPC476028
0.8933	High Similarity	NPC171204
0.8718	High Similarity	NPC52861
0.8701	High Similarity	NPC270126
0.8659	High Similarity	NPC476803
0.8659	High Similarity	NPC476805
0.8649	High Similarity	NPC269206
0.8649	High Similarity	NPC295633
0.8649	High Similarity	NPC58956
0.8625	High Similarity	NPC158756
0.8625	High Similarity	NPC476804
0.859	High Similarity	NPC281132
0.8553	High Similarity	NPC235906
0.8519	High Similarity	NPC470755
0.8514	High Similarity	NPC163003
0.8462	Intermediate Similarity	NPC167881
0.8462	Intermediate Similarity	NPC89128
0.8462	Intermediate Similarity	NPC98557
0.8442	Intermediate Similarity	NPC97516
0.8421	Intermediate Similarity	NPC155587
0.8415	Intermediate Similarity	NPC469910
0.8313	Intermediate Similarity	NPC266957
0.8293	Intermediate Similarity	NPC255307
0.8289	Intermediate Similarity	NPC140287
0.8289	Intermediate Similarity	NPC476355
0.8272	Intermediate Similarity	NPC131669
0.8272	Intermediate Similarity	NPC474703
0.8272	Intermediate Similarity	NPC169575
0.8272	Intermediate Similarity	NPC475989
0.8272	Intermediate Similarity	NPC473390
0.8272	Intermediate Similarity	NPC475947
0.8272	Intermediate Similarity	NPC40746
0.825	Intermediate Similarity	NPC301477
0.825	Intermediate Similarity	NPC281949
0.825	Intermediate Similarity	NPC141810
0.825	Intermediate Similarity	NPC25684
0.825	Intermediate Similarity	NPC24417
0.8228	Intermediate Similarity	NPC178277
0.8228	Intermediate Similarity	NPC617
0.8214	Intermediate Similarity	NPC475819
0.8205	Intermediate Similarity	NPC57744
0.8193	Intermediate Similarity	NPC305475
0.8193	Intermediate Similarity	NPC50637
0.8193	Intermediate Similarity	NPC475461
0.8171	Intermediate Similarity	NPC96259
0.8171	Intermediate Similarity	NPC191476
0.8171	Intermediate Similarity	NPC114979
0.8171	Intermediate Similarity	NPC141193
0.8161	Intermediate Similarity	NPC476267
0.8148	Intermediate Similarity	NPC89555
0.8148	Intermediate Similarity	NPC229825
0.8118	Intermediate Similarity	NPC475971
0.8101	Intermediate Similarity	NPC471465
0.8101	Intermediate Similarity	NPC128276
0.8101	Intermediate Similarity	NPC196653
0.8077	Intermediate Similarity	NPC123360
0.8072	Intermediate Similarity	NPC78089
0.8049	Intermediate Similarity	NPC59097
0.8049	Intermediate Similarity	NPC318468
0.8046	Intermediate Similarity	NPC475302
0.8025	Intermediate Similarity	NPC475481
0.8025	Intermediate Similarity	NPC79277
0.8025	Intermediate Similarity	NPC471325
0.8023	Intermediate Similarity	NPC469368
0.8023	Intermediate Similarity	NPC474232
0.8	Intermediate Similarity	NPC296522
0.8	Intermediate Similarity	NPC144511
0.7976	Intermediate Similarity	NPC150755
0.7976	Intermediate Similarity	NPC469483
0.7976	Intermediate Similarity	NPC107787
0.7975	Intermediate Similarity	NPC320630
0.7975	Intermediate Similarity	NPC41780
0.7975	Intermediate Similarity	NPC7563
0.7975	Intermediate Similarity	NPC187568
0.7975	Intermediate Similarity	NPC476794
0.7975	Intermediate Similarity	NPC116177
0.7975	Intermediate Similarity	NPC65603
0.7975	Intermediate Similarity	NPC470240
0.7955	Intermediate Similarity	NPC140543
0.7955	Intermediate Similarity	NPC471147
0.7949	Intermediate Similarity	NPC138408
0.7949	Intermediate Similarity	NPC193351
0.7949	Intermediate Similarity	NPC226669
0.7931	Intermediate Similarity	NPC284185
0.7927	Intermediate Similarity	NPC85772
0.7907	Intermediate Similarity	NPC166919
0.7895	Intermediate Similarity	NPC472955
0.7875	Intermediate Similarity	NPC267231
0.7875	Intermediate Similarity	NPC108816
0.7875	Intermediate Similarity	NPC93763
0.7865	Intermediate Similarity	NPC475659
0.7848	Intermediate Similarity	NPC474447
0.7841	Intermediate Similarity	NPC165383
0.7821	Intermediate Similarity	NPC15499
0.7821	Intermediate Similarity	NPC259599
0.7821	Intermediate Similarity	NPC474551
0.7821	Intermediate Similarity	NPC117746
0.7821	Intermediate Similarity	NPC294434
0.7821	Intermediate Similarity	NPC474758
0.7816	Intermediate Similarity	NPC179394
0.7816	Intermediate Similarity	NPC475855
0.7816	Intermediate Similarity	NPC312042
0.7816	Intermediate Similarity	NPC253144
0.7816	Intermediate Similarity	NPC144133
0.7805	Intermediate Similarity	NPC42470
0.7805	Intermediate Similarity	NPC470241
0.7778	Intermediate Similarity	NPC19841
0.7778	Intermediate Similarity	NPC182550
0.7778	Intermediate Similarity	NPC230800
0.7778	Intermediate Similarity	NPC473859
0.7765	Intermediate Similarity	NPC279859
0.7765	Intermediate Similarity	NPC38576
0.7763	Intermediate Similarity	NPC199557
0.7738	Intermediate Similarity	NPC115786
0.7738	Intermediate Similarity	NPC159635
0.7733	Intermediate Similarity	NPC194871
0.7727	Intermediate Similarity	NPC150978
0.7727	Intermediate Similarity	NPC70595
0.7727	Intermediate Similarity	NPC74103
0.7727	Intermediate Similarity	NPC123177
0.7722	Intermediate Similarity	NPC329852
0.7722	Intermediate Similarity	NPC324762
0.7711	Intermediate Similarity	NPC35556
0.7711	Intermediate Similarity	NPC173609
0.7701	Intermediate Similarity	NPC151770
0.7692	Intermediate Similarity	NPC135703
0.7692	Intermediate Similarity	NPC474543
0.7692	Intermediate Similarity	NPC238425
0.7692	Intermediate Similarity	NPC472018
0.7692	Intermediate Similarity	NPC471140
0.7683	Intermediate Similarity	NPC223904
0.7683	Intermediate Similarity	NPC276356
0.7667	Intermediate Similarity	NPC471142
0.7667	Intermediate Similarity	NPC477922
0.7662	Intermediate Similarity	NPC69462
0.7654	Intermediate Similarity	NPC474341
0.7654	Intermediate Similarity	NPC218817
0.7654	Intermediate Similarity	NPC11796
0.7647	Intermediate Similarity	NPC261380
0.7647	Intermediate Similarity	NPC38468
0.7647	Intermediate Similarity	NPC165162
0.7647	Intermediate Similarity	NPC50362
0.7647	Intermediate Similarity	NPC33570
0.7647	Intermediate Similarity	NPC319795
0.7647	Intermediate Similarity	NPC21471
0.764	Intermediate Similarity	NPC228451
0.764	Intermediate Similarity	NPC125674
0.764	Intermediate Similarity	NPC475838
0.7632	Intermediate Similarity	NPC470256
0.7625	Intermediate Similarity	NPC68819
0.7619	Intermediate Similarity	NPC116543
0.7619	Intermediate Similarity	NPC272814
0.7619	Intermediate Similarity	NPC215294
0.7619	Intermediate Similarity	NPC250315
0.7614	Intermediate Similarity	NPC473619
0.7609	Intermediate Similarity	NPC208233
0.7595	Intermediate Similarity	NPC48641
0.7595	Intermediate Similarity	NPC472966
0.759	Intermediate Similarity	NPC39411
0.759	Intermediate Similarity	NPC325031
0.759	Intermediate Similarity	NPC207188
0.759	Intermediate Similarity	NPC255580
0.7586	Intermediate Similarity	NPC475906
0.7586	Intermediate Similarity	NPC473715
0.7586	Intermediate Similarity	NPC469631
0.7586	Intermediate Similarity	NPC469628
0.7586	Intermediate Similarity	NPC471047
0.7586	Intermediate Similarity	NPC469653
0.7586	Intermediate Similarity	NPC477128
0.7582	Intermediate Similarity	NPC17585
0.7582	Intermediate Similarity	NPC477921
0.7582	Intermediate Similarity	NPC54731
0.7561	Intermediate Similarity	NPC264227
0.7561	Intermediate Similarity	NPC470239
0.7561	Intermediate Similarity	NPC63649
0.7561	Intermediate Similarity	NPC470244
0.7561	Intermediate Similarity	NPC469690
0.7561	Intermediate Similarity	NPC472965
0.7556	Intermediate Similarity	NPC473316
0.7556	Intermediate Similarity	NPC473330
0.7556	Intermediate Similarity	NPC474247
0.7553	Intermediate Similarity	NPC183571
0.7532	Intermediate Similarity	NPC107130
0.7532	Intermediate Similarity	NPC476591
0.7532	Intermediate Similarity	NPC88877
0.7529	Intermediate Similarity	NPC82297
0.7529	Intermediate Similarity	NPC295799
0.7528	Intermediate Similarity	NPC261607
0.7528	Intermediate Similarity	NPC111114
0.7528	Intermediate Similarity	NPC20713
0.7528	Intermediate Similarity	NPC473321
0.7528	Intermediate Similarity	NPC300312
0.7527	Intermediate Similarity	NPC288876
0.75	Intermediate Similarity	NPC472266
0.75	Intermediate Similarity	NPC475690
0.75	Intermediate Similarity	NPC469414
0.75	Intermediate Similarity	NPC329826
0.75	Intermediate Similarity	NPC244166

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 NPC474760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1993
0.2-0.3	4079
0.3-0.4	2003
0.4-0.5	587
0.5-0.6	248
0.6-0.7	46
0.7-0.8	17
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
0.7647	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1695	Approved
0.7283	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1694	Approved
0.7093	Intermediate Similarity	NPD4269	Approved
0.7093	Intermediate Similarity	NPD5209	Approved
0.7093	Intermediate Similarity	NPD4270	Approved
0.7093	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8039	Approved
0.7045	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5785	Approved
0.7013	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD5369	Approved
0.6966	Remote Similarity	NPD5786	Approved
0.69	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6435	Approved
0.686	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4252	Approved
0.6854	Remote Similarity	NPD5363	Approved
0.6848	Remote Similarity	NPD46	Approved
0.6848	Remote Similarity	NPD6698	Approved
0.6818	Remote Similarity	NPD5362	Discontinued
0.6774	Remote Similarity	NPD7983	Approved
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6701	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4268	Approved
0.6628	Remote Similarity	NPD4271	Approved
0.6593	Remote Similarity	NPD4249	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6101	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6522	Remote Similarity	NPD4250	Approved
0.6458	Remote Similarity	NPD5282	Discontinued
0.6421	Remote Similarity	NPD6411	Approved
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.6389	Remote Similarity	NPD6927	Phase 3
0.6354	Remote Similarity	NPD6399	Phase 3
0.6327	Remote Similarity	NPD7839	Suspended
0.6277	Remote Similarity	NPD6903	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5331	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6222	Remote Similarity	NPD4790	Discontinued
0.6211	Remote Similarity	NPD5370	Suspended
0.619	Remote Similarity	NPD6686	Approved
0.6168	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7838	Discovery
0.6122	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7900	Approved
0.6106	Remote Similarity	NPD8513	Phase 3
0.6106	Remote Similarity	NPD8515	Approved
0.6106	Remote Similarity	NPD8516	Approved
0.6106	Remote Similarity	NPD8517	Approved
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6082	Remote Similarity	NPD5693	Phase 1
0.6082	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6051	Approved
0.604	Remote Similarity	NPD7638	Approved
0.6036	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5979	Remote Similarity	NPD5207	Approved
0.5976	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6053	Discontinued
0.5952	Remote Similarity	NPD229	Approved
0.5946	Remote Similarity	NPD28	Approved
0.5946	Remote Similarity	NPD29	Approved
0.5943	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7902	Approved
0.59	Remote Similarity	NPD5695	Phase 3
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6422	Discontinued
0.5895	Remote Similarity	NPD6098	Approved
0.5889	Remote Similarity	NPD3732	Approved
0.5882	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5696	Approved
0.5875	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD2204	Approved
0.5854	Remote Similarity	NPD3197	Phase 1
0.5851	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6008	Approved
0.5847	Remote Similarity	NPD8074	Phase 3
0.5806	Remote Similarity	NPD3667	Approved
0.5802	Remote Similarity	NPD368	Approved
0.58	Remote Similarity	NPD6001	Approved
0.58	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD3172	Approved
0.5784	Remote Similarity	NPD6083	Phase 2
0.5784	Remote Similarity	NPD6084	Phase 2
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.578	Remote Similarity	NPD2067	Discontinued
0.5773	Remote Similarity	NPD5208	Approved
0.5758	Remote Similarity	NPD8034	Phase 2
0.5758	Remote Similarity	NPD8035	Phase 2
0.5753	Remote Similarity	NPD5343	Approved
0.5729	Remote Similarity	NPD3618	Phase 1
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.5694	Remote Similarity	NPD3174	Discontinued
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6413	Approved
0.5688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4228	Discovery
0.5684	Remote Similarity	NPD4786	Approved
0.5684	Remote Similarity	NPD3666	Approved
0.5684	Remote Similarity	NPD3665	Phase 1
0.5684	Remote Similarity	NPD3133	Approved
0.5684	Remote Similarity	NPD3668	Phase 3
0.5673	Remote Similarity	NPD6648	Approved
0.567	Remote Similarity	NPD3573	Approved
0.5657	Remote Similarity	NPD3673	Approved
0.5657	Remote Similarity	NPD5692	Phase 3
0.5657	Remote Similarity	NPD3672	Approved
0.5648	Remote Similarity	NPD5697	Approved
0.5648	Remote Similarity	NPD5701	Approved
0.5638	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5344	Discontinued
0.5604	Remote Similarity	NPD4756	Discovery
0.56	Remote Similarity	NPD7515	Phase 2
0.56	Remote Similarity	NPD5281	Approved
0.56	Remote Similarity	NPD5694	Approved
0.56	Remote Similarity	NPD5284	Approved
0.56	Remote Similarity	NPD6050	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