NPASS Compound

Structure

NPC182136 OpenBabel07101718282D 23 25 0 0 1 0 0 0 0 0999 V2000 2.4487 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1808 3.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1808 4.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 1 0 0 0 16 21 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.01
LogD:	3.926
LogS:	-4.218
# Rotatable Bonds:	2
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	4.613
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.626
MDCK Permeability:	2.4606959414086305e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.265
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.501
Plasma Protein Binding (PPB):	92.64818572998047%
Volume Distribution (VD):	1.157
Pgp-substrate:	13.545391082763672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.239
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.509
CYP2C9-inhibitor:	0.484
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.782
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	11.354
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.196
Carcinogencity:	0.464
Eye Corrosion:	0.343
Eye Irritation:	0.536
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC182136

Natural Product ID:	NPC182136
*Common Name:**	XMFHYLXGTZLYKM-XHNMEYTFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XMFHYLXGTZLYKM-XHNMEYTFSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13-15(7-6-14-8-11-23-18(14)22)20(4)10-5-9-19(2,3)17(20)12-16(13)21/h6-8,15-17,21H,1,5,9-12H2,2-4H3/b7-6+/t15-,16-,17-,20+/m0/s1
SMILES:	C=C1[C@@H](O)C[C@@H]2[C@]([C@H]1/C=C/C1=CCOC1=O)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622819
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:0001538] Diterpene lactones

*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
NPO32565	hedychium longipetalum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351042]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6.52	ug.mL-1	PMID[491484]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	14.83	ug.mL-1	PMID[491484]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.53	ug.mL-1	PMID[491484]

☑ 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 NPC182136 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	178
0.1-0.2	910
0.2-0.3	3491
0.3-0.4	7469
0.4-0.5	15037
0.5-0.6	8232
0.6-0.7	5600
0.7-0.8	1551
0.8-0.85	173
0.85-0.9	39
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC310479
0.954	High Similarity	NPC205034
0.954	High Similarity	NPC162615
0.954	High Similarity	NPC152778
0.9438	High Similarity	NPC473153
0.931	High Similarity	NPC221111
0.931	High Similarity	NPC280149
0.9222	High Similarity	NPC16967
0.9213	High Similarity	NPC191521
0.9213	High Similarity	NPC470255
0.9195	High Similarity	NPC50488
0.9195	High Similarity	NPC474396
0.9022	High Similarity	NPC474440
0.8941	High Similarity	NPC311070
0.8876	High Similarity	NPC78973
0.8851	High Similarity	NPC131813
0.8851	High Similarity	NPC329692
0.8791	High Similarity	NPC57117
0.8778	High Similarity	NPC472811
0.8778	High Similarity	NPC72845
0.8696	High Similarity	NPC209355
0.8681	High Similarity	NPC139692
0.8681	High Similarity	NPC472812
0.8681	High Similarity	NPC53555
0.8602	High Similarity	NPC134072
0.8602	High Similarity	NPC242848
0.8602	High Similarity	NPC234993
0.8588	High Similarity	NPC268827
0.8571	High Similarity	NPC472814
0.8571	High Similarity	NPC177037
0.8539	High Similarity	NPC473891
0.8523	High Similarity	NPC109528
0.8523	High Similarity	NPC471795
0.8523	High Similarity	NPC86316
0.8523	High Similarity	NPC106416
0.8511	High Similarity	NPC474343
0.8506	High Similarity	NPC42476
0.8506	High Similarity	NPC79945
0.8506	High Similarity	NPC57370
0.8488	Intermediate Similarity	NPC159148
0.8452	Intermediate Similarity	NPC189206
0.8444	Intermediate Similarity	NPC472810
0.8444	Intermediate Similarity	NPC472809
0.8421	Intermediate Similarity	NPC108368
0.8421	Intermediate Similarity	NPC159763
0.8421	Intermediate Similarity	NPC57079
0.8421	Intermediate Similarity	NPC278386
0.8421	Intermediate Similarity	NPC124512
0.8409	Intermediate Similarity	NPC302360
0.8409	Intermediate Similarity	NPC96055
0.8404	Intermediate Similarity	NPC190713
0.8372	Intermediate Similarity	NPC10636
0.8372	Intermediate Similarity	NPC281880
0.837	Intermediate Similarity	NPC329842
0.8353	Intermediate Similarity	NPC184737
0.8351	Intermediate Similarity	NPC114540
0.8351	Intermediate Similarity	NPC32577
0.8351	Intermediate Similarity	NPC155332
0.8333	Intermediate Similarity	NPC4509
0.8333	Intermediate Similarity	NPC266955
0.8333	Intermediate Similarity	NPC312561
0.8316	Intermediate Similarity	NPC208094
0.8316	Intermediate Similarity	NPC99726
0.8316	Intermediate Similarity	NPC73911
0.8316	Intermediate Similarity	NPC141401
0.8315	Intermediate Similarity	NPC65661
0.8298	Intermediate Similarity	NPC276110
0.8298	Intermediate Similarity	NPC472441
0.8295	Intermediate Similarity	NPC472377
0.828	Intermediate Similarity	NPC115021
0.8276	Intermediate Similarity	NPC170303
0.8261	Intermediate Similarity	NPC51486
0.8247	Intermediate Similarity	NPC115899
0.8247	Intermediate Similarity	NPC303559
0.8229	Intermediate Similarity	NPC278673
0.8229	Intermediate Similarity	NPC316598
0.8229	Intermediate Similarity	NPC218107
0.8229	Intermediate Similarity	NPC92275
0.8229	Intermediate Similarity	NPC473154
0.8222	Intermediate Similarity	NPC471219
0.8211	Intermediate Similarity	NPC301534
0.8211	Intermediate Similarity	NPC165632
0.8211	Intermediate Similarity	NPC250757
0.8202	Intermediate Similarity	NPC32223
0.8191	Intermediate Similarity	NPC201725
0.8191	Intermediate Similarity	NPC105490
0.8191	Intermediate Similarity	NPC469491
0.8191	Intermediate Similarity	NPC469697
0.8182	Intermediate Similarity	NPC16321
0.8182	Intermediate Similarity	NPC471218
0.8172	Intermediate Similarity	NPC477783
0.8172	Intermediate Similarity	NPC212948
0.8163	Intermediate Similarity	NPC475038
0.8163	Intermediate Similarity	NPC109195
0.8152	Intermediate Similarity	NPC174342
0.8152	Intermediate Similarity	NPC262858
0.8152	Intermediate Similarity	NPC470734
0.8152	Intermediate Similarity	NPC5509
0.8152	Intermediate Similarity	NPC146554
0.8152	Intermediate Similarity	NPC82876
0.8152	Intermediate Similarity	NPC472240
0.8152	Intermediate Similarity	NPC251528
0.8144	Intermediate Similarity	NPC474012
0.8144	Intermediate Similarity	NPC477720
0.8144	Intermediate Similarity	NPC476299
0.8144	Intermediate Similarity	NPC201406
0.8144	Intermediate Similarity	NPC38855
0.8132	Intermediate Similarity	NPC166857
0.8132	Intermediate Similarity	NPC471796
0.8125	Intermediate Similarity	NPC205143
0.8125	Intermediate Similarity	NPC253826
0.8125	Intermediate Similarity	NPC475709
0.8111	Intermediate Similarity	NPC30984
0.8111	Intermediate Similarity	NPC476602
0.8111	Intermediate Similarity	NPC473251
0.8111	Intermediate Similarity	NPC42586
0.8111	Intermediate Similarity	NPC474013
0.8111	Intermediate Similarity	NPC329630
0.8105	Intermediate Similarity	NPC295347
0.8105	Intermediate Similarity	NPC183012
0.81	Intermediate Similarity	NPC218158
0.81	Intermediate Similarity	NPC81630
0.81	Intermediate Similarity	NPC266570
0.809	Intermediate Similarity	NPC476927
0.809	Intermediate Similarity	NPC474809
0.8085	Intermediate Similarity	NPC472303
0.8085	Intermediate Similarity	NPC7349
0.8085	Intermediate Similarity	NPC472640
0.8085	Intermediate Similarity	NPC472641
0.8085	Intermediate Similarity	NPC214697
0.8085	Intermediate Similarity	NPC38232
0.8081	Intermediate Similarity	NPC471938
0.8081	Intermediate Similarity	NPC297617
0.8081	Intermediate Similarity	NPC45897
0.8081	Intermediate Similarity	NPC23584
0.8068	Intermediate Similarity	NPC142163
0.8065	Intermediate Similarity	NPC281942
0.8065	Intermediate Similarity	NPC477782
0.8065	Intermediate Similarity	NPC472642
0.8065	Intermediate Similarity	NPC232426
0.8061	Intermediate Similarity	NPC471412
0.8058	Intermediate Similarity	NPC474315
0.8046	Intermediate Similarity	NPC242767
0.8046	Intermediate Similarity	NPC100906
0.8043	Intermediate Similarity	NPC474629
0.8043	Intermediate Similarity	NPC472378
0.8043	Intermediate Similarity	NPC473879
0.8043	Intermediate Similarity	NPC104560
0.8043	Intermediate Similarity	NPC229612
0.8043	Intermediate Similarity	NPC7280
0.8043	Intermediate Similarity	NPC291665
0.8041	Intermediate Similarity	NPC275086
0.8041	Intermediate Similarity	NPC325229
0.8021	Intermediate Similarity	NPC162346
0.8	Intermediate Similarity	NPC119562
0.8	Intermediate Similarity	NPC476186
0.8	Intermediate Similarity	NPC470800
0.8	Intermediate Similarity	NPC104925
0.8	Intermediate Similarity	NPC102048
0.8	Intermediate Similarity	NPC279410
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC306951
0.8	Intermediate Similarity	NPC298973
0.8	Intermediate Similarity	NPC477130
0.8	Intermediate Similarity	NPC474693
0.8	Intermediate Similarity	NPC471937
0.798	Intermediate Similarity	NPC11956
0.798	Intermediate Similarity	NPC273005
0.798	Intermediate Similarity	NPC31058
0.798	Intermediate Similarity	NPC476081
0.798	Intermediate Similarity	NPC471914
0.798	Intermediate Similarity	NPC469606
0.7979	Intermediate Similarity	NPC110923
0.7979	Intermediate Similarity	NPC186363
0.7979	Intermediate Similarity	NPC303697
0.7979	Intermediate Similarity	NPC141831
0.7979	Intermediate Similarity	NPC78594
0.7979	Intermediate Similarity	NPC74296
0.7979	Intermediate Similarity	NPC289479
0.7979	Intermediate Similarity	NPC233345
0.7978	Intermediate Similarity	NPC94200
0.7978	Intermediate Similarity	NPC224455
0.7978	Intermediate Similarity	NPC200513
0.7978	Intermediate Similarity	NPC256112
0.7978	Intermediate Similarity	NPC2524
0.7959	Intermediate Similarity	NPC16601
0.7959	Intermediate Similarity	NPC471413
0.7959	Intermediate Similarity	NPC117685
0.7959	Intermediate Similarity	NPC476767
0.7959	Intermediate Similarity	NPC251680
0.7959	Intermediate Similarity	NPC472644
0.7959	Intermediate Similarity	NPC324841
0.7959	Intermediate Similarity	NPC227865
0.7957	Intermediate Similarity	NPC36668
0.7957	Intermediate Similarity	NPC79027
0.7957	Intermediate Similarity	NPC177141
0.7957	Intermediate Similarity	NPC118011
0.7957	Intermediate Similarity	NPC314727
0.7957	Intermediate Similarity	NPC16265
0.7941	Intermediate Similarity	NPC470024

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 NPC182136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1065
0.2-0.3	3382
0.3-0.4	2745
0.4-0.5	1260
0.5-0.6	297
0.6-0.7	225
0.7-0.8	21
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD4225	Approved
0.7978	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD7639	Approved
0.7857	Intermediate Similarity	NPD7638	Approved
0.7604	Intermediate Similarity	NPD7637	Suspended
0.7419	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8264	Approved
0.7364	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD1694	Approved
0.7282	Intermediate Similarity	NPD7632	Discontinued
0.7264	Intermediate Similarity	NPD6686	Approved
0.7255	Intermediate Similarity	NPD6648	Approved
0.7184	Intermediate Similarity	NPD5344	Discontinued
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5785	Approved
0.7128	Intermediate Similarity	NPD6695	Phase 3
0.71	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD6926	Approved
0.7079	Intermediate Similarity	NPD6924	Approved
0.7071	Intermediate Similarity	NPD7515	Phase 2
0.7071	Intermediate Similarity	NPD6411	Approved
0.7071	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD6929	Approved
0.7053	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7152	Approved
0.7045	Intermediate Similarity	NPD7150	Approved
0.7045	Intermediate Similarity	NPD7151	Approved
0.7021	Intermediate Similarity	NPD5209	Approved
0.7021	Intermediate Similarity	NPD3667	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7514	Phase 3
0.6989	Remote Similarity	NPD6931	Approved
0.6989	Remote Similarity	NPD6930	Phase 2
0.6989	Remote Similarity	NPD7332	Phase 2
0.6979	Remote Similarity	NPD1696	Phase 3
0.6957	Remote Similarity	NPD7145	Approved
0.6944	Remote Similarity	NPD6899	Approved
0.6944	Remote Similarity	NPD6881	Approved
0.6944	Remote Similarity	NPD6011	Approved
0.6932	Remote Similarity	NPD7143	Approved
0.6932	Remote Similarity	NPD7144	Approved
0.6923	Remote Similarity	NPD6933	Approved
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6902	Approved
0.6907	Remote Similarity	NPD6684	Approved
0.6907	Remote Similarity	NPD5279	Phase 3
0.6907	Remote Similarity	NPD7146	Approved
0.6907	Remote Similarity	NPD7334	Approved
0.6907	Remote Similarity	NPD6409	Approved
0.6907	Remote Similarity	NPD7521	Approved
0.6907	Remote Similarity	NPD5330	Approved
0.6893	Remote Similarity	NPD7902	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD4786	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD6101	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6051	Approved
0.6869	Remote Similarity	NPD5328	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6925	Approved
0.6848	Remote Similarity	NPD5776	Phase 2
0.6837	Remote Similarity	NPD7750	Discontinued
0.6837	Remote Similarity	NPD7524	Approved
0.6837	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD6923	Approved
0.6818	Remote Similarity	NPD7290	Approved
0.6818	Remote Similarity	NPD6922	Approved
0.6813	Remote Similarity	NPD6942	Approved
0.6813	Remote Similarity	NPD8039	Approved
0.6813	Remote Similarity	NPD7339	Approved
0.681	Remote Similarity	NPD7503	Approved
0.6809	Remote Similarity	NPD7509	Discontinued
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5222	Approved
0.6792	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6757	Remote Similarity	NPD6617	Approved
0.6757	Remote Similarity	NPD6869	Approved
0.6757	Remote Similarity	NPD6649	Approved
0.6757	Remote Similarity	NPD6847	Approved
0.6757	Remote Similarity	NPD6650	Approved
0.6757	Remote Similarity	NPD8130	Phase 1
0.6735	Remote Similarity	NPD4623	Approved
0.6735	Remote Similarity	NPD4519	Discontinued
0.6731	Remote Similarity	NPD5173	Approved
0.6731	Remote Similarity	NPD6083	Phase 2
0.6731	Remote Similarity	NPD6084	Phase 2
0.6702	Remote Similarity	NPD7645	Phase 2
0.6702	Remote Similarity	NPD4195	Approved
0.6697	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD7327	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6696	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6932	Approved
0.6638	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6633	Remote Similarity	NPD6893	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5363	Approved
0.6632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4695	Discontinued
0.6632	Remote Similarity	NPD7525	Registered
0.6628	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5286	Approved
0.6604	Remote Similarity	NPD5285	Approved
0.6604	Remote Similarity	NPD4696	Approved
0.6602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7900	Approved
0.66	Remote Similarity	NPD5737	Approved
0.66	Remote Similarity	NPD6672	Approved
0.6598	Remote Similarity	NPD5362	Discontinued
0.6598	Remote Similarity	NPD7154	Phase 3
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4194	Approved
0.6588	Remote Similarity	NPD4191	Approved
0.6588	Remote Similarity	NPD4193	Approved
0.6588	Remote Similarity	NPD4192	Approved
0.6581	Remote Similarity	NPD8294	Approved
0.6581	Remote Similarity	NPD8377	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6569	Remote Similarity	NPD5693	Phase 1
0.6569	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD7087	Discontinued
0.6569	Remote Similarity	NPD5281	Approved
0.6562	Remote Similarity	NPD6898	Phase 1
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8378	Approved
0.6525	Remote Similarity	NPD8380	Approved
0.6525	Remote Similarity	NPD8335	Approved
0.6525	Remote Similarity	NPD8379	Approved
0.6525	Remote Similarity	NPD8296	Approved
0.6522	Remote Similarity	NPD6868	Approved
0.6509	Remote Similarity	NPD5290	Discontinued
0.6509	Remote Similarity	NPD5696	Approved
0.6491	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD5224	Approved
0.6481	Remote Similarity	NPD5225	Approved
0.6481	Remote Similarity	NPD4633	Approved
0.6481	Remote Similarity	NPD5226	Approved
0.6476	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD46	Approved
0.6471	Remote Similarity	NPD5207	Approved
0.6466	Remote Similarity	NPD6317	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4820	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6449	Remote Similarity	NPD6404	Discontinued
0.6446	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5331	Approved
0.6422	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD6647	Phase 2
0.6422	Remote Similarity	NPD5174	Approved
0.6421	Remote Similarity	NPD4271	Approved
0.6421	Remote Similarity	NPD4268	Approved
0.6415	Remote Similarity	NPD4755	Approved
0.641	Remote Similarity	NPD6314	Approved
0.641	Remote Similarity	NPD6335	Approved
0.641	Remote Similarity	NPD6313	Approved
0.6408	Remote Similarity	NPD8035	Phase 2
0.6408	Remote Similarity	NPD5694	Approved
0.6408	Remote Similarity	NPD8034	Phase 2
0.6396	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4790	Discontinued

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