NPASS Compound

Structure

NPC16321 OpenBabel07101718232D 23 25 0 0 1 0 0 0 0 0999 V2000 1.9487 4.7024 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 5.9128 3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 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 2.8147 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0388 2.5873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 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 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 1 0 0 0 16 21 1 0 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:	5.365
LogD:	4.578
LogS:	-4.336
# 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:	0.708
Synthetic Accessibility Score:	4.418
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:	-4.676
MDCK Permeability:	3.1591822335030884e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	97.9383773803711%
Volume Distribution (VD):	2.259
Pgp-substrate:	2.447869300842285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.66
CYP2D6-inhibitor:	0.384
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	13.084
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.919
Carcinogencity:	0.917
Eye Corrosion:	0.022
Eye Irritation:	0.634
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC16321

Natural Product ID:	NPC16321
*Common Name:**	Zerumin
IUPAC Name:	4-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-3-hydroxy-2H-furan-5-one
Synonyms:	Zerumin
Standard InCHIKey:	OEKNHOLIWSBXIC-NEMSWOBWSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13-6-9-17-19(2,3)10-5-11-20(17,4)15(13)8-7-14-16(21)12-23-18(14)22/h7-8,15,17,21H,1,5-6,9-12H2,2-4H3/b8-7+/t15-,17-,20+/m0/s1
SMILES:	C=C1CC[C@@H]2[C@]([C@H]1/C=C/C1=C(O)COC1=O)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098958
PubChem CID:	54734314
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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO22901	Curcuma comosa	Species	Zingiberaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	FC	=	1.0	n.a.	PMID[484565]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	87.5	%	PMID[484565]

☑ 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 NPC16321 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	158
0.1-0.2	977
0.2-0.3	4817
0.3-0.4	13857
0.4-0.5	11413
0.5-0.6	8686
0.6-0.7	2512
0.7-0.8	259
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8961	High Similarity	NPC4509
0.8537	High Similarity	NPC94200
0.8313	Intermediate Similarity	NPC268122
0.8235	Intermediate Similarity	NPC329630
0.8214	Intermediate Similarity	NPC118423
0.8182	Intermediate Similarity	NPC182136
0.8182	Intermediate Similarity	NPC310479
0.8132	Intermediate Similarity	NPC473153
0.8118	Intermediate Similarity	NPC470800
0.8068	Intermediate Similarity	NPC79027
0.8	Intermediate Similarity	NPC205034
0.8	Intermediate Similarity	NPC162615
0.8	Intermediate Similarity	NPC42476
0.8	Intermediate Similarity	NPC152778
0.7978	Intermediate Similarity	NPC280149
0.7978	Intermediate Similarity	NPC221111
0.7975	Intermediate Similarity	NPC181587
0.7935	Intermediate Similarity	NPC16967
0.7931	Intermediate Similarity	NPC168248
0.7912	Intermediate Similarity	NPC191521
0.7857	Intermediate Similarity	NPC268827
0.7841	Intermediate Similarity	NPC473891
0.7826	Intermediate Similarity	NPC209355
0.7826	Intermediate Similarity	NPC295347
0.7802	Intermediate Similarity	NPC53555
0.7802	Intermediate Similarity	NPC469939
0.7802	Intermediate Similarity	NPC242069
0.7792	Intermediate Similarity	NPC185587
0.7791	Intermediate Similarity	NPC311070
0.7753	Intermediate Similarity	NPC196407
0.7717	Intermediate Similarity	NPC470255
0.7711	Intermediate Similarity	NPC54996
0.7692	Intermediate Similarity	NPC303697
0.7667	Intermediate Similarity	NPC474844
0.7667	Intermediate Similarity	NPC471654
0.766	Intermediate Similarity	NPC208094
0.7629	Intermediate Similarity	NPC23584
0.7619	Intermediate Similarity	NPC184737
0.7614	Intermediate Similarity	NPC30984
0.7614	Intermediate Similarity	NPC86316
0.7614	Intermediate Similarity	NPC106416
0.7614	Intermediate Similarity	NPC65661
0.7614	Intermediate Similarity	NPC217394
0.7614	Intermediate Similarity	NPC471795
0.7586	Intermediate Similarity	NPC474976
0.7586	Intermediate Similarity	NPC49208
0.7586	Intermediate Similarity	NPC474790
0.7579	Intermediate Similarity	NPC474440
0.7579	Intermediate Similarity	NPC181147
0.7561	Intermediate Similarity	NPC20025
0.7561	Intermediate Similarity	NPC104644
0.7556	Intermediate Similarity	NPC472302
0.7556	Intermediate Similarity	NPC474629
0.7532	Intermediate Similarity	NPC329698
0.7529	Intermediate Similarity	NPC190211
0.7528	Intermediate Similarity	NPC131813
0.7528	Intermediate Similarity	NPC471219
0.7526	Intermediate Similarity	NPC11956
0.75	Intermediate Similarity	NPC473825
0.75	Intermediate Similarity	NPC189206
0.75	Intermediate Similarity	NPC96055
0.7473	Intermediate Similarity	NPC82876
0.7473	Intermediate Similarity	NPC50488
0.7473	Intermediate Similarity	NPC474396
0.7471	Intermediate Similarity	NPC200513
0.7471	Intermediate Similarity	NPC471218
0.7444	Intermediate Similarity	NPC125925
0.7444	Intermediate Similarity	NPC75315
0.7444	Intermediate Similarity	NPC163016
0.7442	Intermediate Similarity	NPC233332
0.7436	Intermediate Similarity	NPC107258
0.7423	Intermediate Similarity	NPC303559
0.7412	Intermediate Similarity	NPC105197
0.7396	Intermediate Similarity	NPC159763
0.7396	Intermediate Similarity	NPC278386
0.7396	Intermediate Similarity	NPC124512
0.7391	Intermediate Similarity	NPC78973
0.7391	Intermediate Similarity	NPC51486
0.7386	Intermediate Similarity	NPC469
0.7386	Intermediate Similarity	NPC23748
0.7363	Intermediate Similarity	NPC472810
0.7363	Intermediate Similarity	NPC472809
0.734	Intermediate Similarity	NPC469491
0.7333	Intermediate Similarity	NPC329692
0.7327	Intermediate Similarity	NPC473482
0.7327	Intermediate Similarity	NPC475418
0.7327	Intermediate Similarity	NPC318363
0.732	Intermediate Similarity	NPC477720
0.732	Intermediate Similarity	NPC38855
0.7317	Intermediate Similarity	NPC133253
0.7312	Intermediate Similarity	NPC472811
0.7312	Intermediate Similarity	NPC72845
0.7312	Intermediate Similarity	NPC177037
0.7312	Intermediate Similarity	NPC472814
0.7308	Intermediate Similarity	NPC226066
0.7303	Intermediate Similarity	NPC318515
0.73	Intermediate Similarity	NPC477125
0.7294	Intermediate Similarity	NPC262747
0.7292	Intermediate Similarity	NPC205143
0.7292	Intermediate Similarity	NPC73911
0.7283	Intermediate Similarity	NPC177141
0.7283	Intermediate Similarity	NPC174342
0.7283	Intermediate Similarity	NPC284561
0.7283	Intermediate Similarity	NPC251528
0.7283	Intermediate Similarity	NPC5509
0.7273	Intermediate Similarity	NPC469804
0.7273	Intermediate Similarity	NPC469806
0.7273	Intermediate Similarity	NPC324170
0.7273	Intermediate Similarity	NPC469805
0.7273	Intermediate Similarity	NPC469799
0.7262	Intermediate Similarity	NPC65650
0.7255	Intermediate Similarity	NPC475065
0.7253	Intermediate Similarity	NPC312561
0.7253	Intermediate Similarity	NPC471796
0.7253	Intermediate Similarity	NPC476600
0.7241	Intermediate Similarity	NPC469797
0.7241	Intermediate Similarity	NPC10636
0.7241	Intermediate Similarity	NPC469798
0.7234	Intermediate Similarity	NPC139692
0.7234	Intermediate Similarity	NPC156553
0.7234	Intermediate Similarity	NPC472812
0.7229	Intermediate Similarity	NPC276336
0.7229	Intermediate Similarity	NPC16349
0.7229	Intermediate Similarity	NPC222244
0.7228	Intermediate Similarity	NPC329048
0.7228	Intermediate Similarity	NPC330011
0.7222	Intermediate Similarity	NPC35933
0.7222	Intermediate Similarity	NPC42586
0.7222	Intermediate Similarity	NPC189311
0.7222	Intermediate Similarity	NPC473251
0.7222	Intermediate Similarity	NPC474013
0.7216	Intermediate Similarity	NPC278673
0.7209	Intermediate Similarity	NPC474816
0.7209	Intermediate Similarity	NPC209135
0.7204	Intermediate Similarity	NPC212679
0.7204	Intermediate Similarity	NPC273199
0.7204	Intermediate Similarity	NPC477782
0.7204	Intermediate Similarity	NPC469595
0.7204	Intermediate Similarity	NPC220454
0.72	Intermediate Similarity	NPC200861
0.72	Intermediate Similarity	NPC472822
0.7191	Intermediate Similarity	NPC477124
0.7191	Intermediate Similarity	NPC472377
0.7191	Intermediate Similarity	NPC193198
0.7191	Intermediate Similarity	NPC3856
0.7191	Intermediate Similarity	NPC279639
0.7191	Intermediate Similarity	NPC474193
0.7191	Intermediate Similarity	NPC12283
0.7188	Intermediate Similarity	NPC260796
0.7179	Intermediate Similarity	NPC44343
0.7179	Intermediate Similarity	NPC179087
0.7179	Intermediate Similarity	NPC210303
0.7176	Intermediate Similarity	NPC474463
0.7174	Intermediate Similarity	NPC473879
0.7172	Intermediate Similarity	NPC472552
0.7172	Intermediate Similarity	NPC114540
0.7172	Intermediate Similarity	NPC32577
0.7172	Intermediate Similarity	NPC155332
0.7159	Intermediate Similarity	NPC170303
0.7159	Intermediate Similarity	NPC40228
0.7159	Intermediate Similarity	NPC14203
0.7159	Intermediate Similarity	NPC229584
0.7159	Intermediate Similarity	NPC25554
0.7158	Intermediate Similarity	NPC57117
0.7158	Intermediate Similarity	NPC477129
0.7158	Intermediate Similarity	NPC477130
0.7158	Intermediate Similarity	NPC469697
0.7157	Intermediate Similarity	NPC50124
0.7143	Intermediate Similarity	NPC75485
0.7143	Intermediate Similarity	NPC470686
0.7143	Intermediate Similarity	NPC168975
0.7143	Intermediate Similarity	NPC211892
0.7129	Intermediate Similarity	NPC82251
0.7129	Intermediate Similarity	NPC471206
0.7128	Intermediate Similarity	NPC329842
0.7128	Intermediate Similarity	NPC477783
0.7126	Intermediate Similarity	NPC233295
0.7126	Intermediate Similarity	NPC242767
0.7125	Intermediate Similarity	NPC191233
0.7125	Intermediate Similarity	NPC259156
0.7125	Intermediate Similarity	NPC242945
0.7125	Intermediate Similarity	NPC255781
0.7113	Intermediate Similarity	NPC110937
0.7113	Intermediate Similarity	NPC202705
0.7113	Intermediate Similarity	NPC231751
0.7111	Intermediate Similarity	NPC32223
0.7111	Intermediate Similarity	NPC475100
0.7111	Intermediate Similarity	NPC149869
0.7108	Intermediate Similarity	NPC21944
0.7108	Intermediate Similarity	NPC257618
0.7097	Intermediate Similarity	NPC210216
0.7097	Intermediate Similarity	NPC470734
0.7083	Intermediate Similarity	NPC276110
0.7079	Intermediate Similarity	NPC474028
0.7079	Intermediate Similarity	NPC474439
0.7073	Intermediate Similarity	NPC232812
0.7071	Intermediate Similarity	NPC472554
0.7071	Intermediate Similarity	NPC198992
0.7059	Intermediate Similarity	NPC67321
0.7059	Intermediate Similarity	NPC187435

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 NPC16321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1070
0.2-0.3	4013
0.3-0.4	2783
0.4-0.5	774
0.5-0.6	297
0.6-0.7	72
0.7-0.8	2
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
0.7471	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4191	Approved
0.7051	Intermediate Similarity	NPD4192	Approved
0.7051	Intermediate Similarity	NPD4194	Approved
0.7051	Intermediate Similarity	NPD4193	Approved
0.6947	Remote Similarity	NPD7637	Suspended
0.6923	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6686	Approved
0.6703	Remote Similarity	NPD5209	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6552	Remote Similarity	NPD4058	Approved
0.6489	Remote Similarity	NPD1694	Approved
0.6486	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD6648	Approved
0.6444	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD7503	Approved
0.6404	Remote Similarity	NPD6933	Approved
0.6395	Remote Similarity	NPD7143	Approved
0.6395	Remote Similarity	NPD7144	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4687	Approved
0.6354	Remote Similarity	NPD7524	Approved
0.6327	Remote Similarity	NPD6698	Approved
0.6327	Remote Similarity	NPD46	Approved
0.6322	Remote Similarity	NPD7152	Approved
0.6322	Remote Similarity	NPD7151	Approved
0.6322	Remote Similarity	NPD5276	Approved
0.6322	Remote Similarity	NPD7150	Approved
0.6304	Remote Similarity	NPD7332	Phase 2
0.6304	Remote Similarity	NPD7514	Phase 3
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8264	Approved
0.6289	Remote Similarity	NPD6903	Approved
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4137	Phase 3
0.6279	Remote Similarity	NPD6923	Approved
0.6279	Remote Similarity	NPD6922	Approved
0.6264	Remote Similarity	NPD7145	Approved
0.6263	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD6902	Approved
0.6224	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4691	Approved
0.6207	Remote Similarity	NPD4747	Approved
0.6203	Remote Similarity	NPD4219	Approved
0.62	Remote Similarity	NPD6399	Phase 3
0.618	Remote Similarity	NPD5733	Approved
0.618	Remote Similarity	NPD6926	Approved
0.618	Remote Similarity	NPD6924	Approved
0.6162	Remote Similarity	NPD5785	Approved
0.6162	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD5776	Phase 2
0.6154	Remote Similarity	NPD6932	Approved
0.6154	Remote Similarity	NPD6925	Approved
0.614	Remote Similarity	NPD7328	Approved
0.614	Remote Similarity	NPD7327	Approved
0.6139	Remote Similarity	NPD7748	Approved
0.6129	Remote Similarity	NPD4695	Discontinued
0.6121	Remote Similarity	NPD8033	Approved
0.6117	Remote Similarity	NPD6083	Phase 2
0.6117	Remote Similarity	NPD6084	Phase 2
0.6105	Remote Similarity	NPD6695	Phase 3
0.61	Remote Similarity	NPD5281	Approved
0.61	Remote Similarity	NPD6411	Approved
0.61	Remote Similarity	NPD5284	Approved
0.61	Remote Similarity	NPD5694	Approved
0.6091	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7516	Approved
0.6082	Remote Similarity	NPD4519	Discontinued
0.6082	Remote Similarity	NPD4623	Approved
0.6082	Remote Similarity	NPD5279	Phase 3
0.6078	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD5696	Approved
0.6042	Remote Similarity	NPD3133	Approved
0.6042	Remote Similarity	NPD3665	Phase 1
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD5778	Approved
0.604	Remote Similarity	NPD5779	Approved
0.6038	Remote Similarity	NPD7632	Discontinued
0.6034	Remote Similarity	NPD8377	Approved
0.6034	Remote Similarity	NPD8294	Approved
0.6022	Remote Similarity	NPD6929	Approved
0.6022	Remote Similarity	NPD4195	Approved
0.602	Remote Similarity	NPD3573	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD3667	Approved
0.5983	Remote Similarity	NPD8380	Approved
0.5983	Remote Similarity	NPD8378	Approved
0.5983	Remote Similarity	NPD8296	Approved
0.5983	Remote Similarity	NPD8379	Approved
0.5983	Remote Similarity	NPD8335	Approved
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD5208	Approved
0.5957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6931	Approved
0.5957	Remote Similarity	NPD6930	Phase 2
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD7983	Approved
0.5938	Remote Similarity	NPD7154	Phase 3
0.5926	Remote Similarity	NPD5909	Discontinued
0.5922	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6049	Phase 2
0.5922	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3618	Phase 1
0.5917	Remote Similarity	NPD7507	Approved
0.5914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4198	Discontinued
0.59	Remote Similarity	NPD6080	Approved
0.59	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6673	Approved
0.59	Remote Similarity	NPD6904	Approved
0.59	Remote Similarity	NPD6101	Approved
0.5895	Remote Similarity	NPD6898	Phase 1
0.5876	Remote Similarity	NPD4786	Approved
0.5872	Remote Similarity	NPD6640	Phase 3
0.587	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7750	Discontinued
0.5851	Remote Similarity	NPD6683	Phase 2
0.5841	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5826	Remote Similarity	NPD2629	Approved
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6412	Phase 2
0.5818	Remote Similarity	NPD5697	Approved
0.5816	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD1696	Phase 3
0.5806	Remote Similarity	NPD7260	Phase 2
0.5804	Remote Similarity	NPD6371	Approved
0.5804	Remote Similarity	NPD2067	Discontinued
0.5795	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4632	Approved
0.5789	Remote Similarity	NPD7509	Discontinued
0.5784	Remote Similarity	NPD6079	Approved
0.5773	Remote Similarity	NPD3971	Phase 1
0.5773	Remote Similarity	NPD5362	Discontinued
0.5773	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7319	Approved
0.5769	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6899	Approved
0.5766	Remote Similarity	NPD6881	Approved
0.5766	Remote Similarity	NPD6011	Approved
0.5761	Remote Similarity	NPD6942	Approved
0.5761	Remote Similarity	NPD7339	Approved
0.5758	Remote Similarity	NPD6098	Approved
0.5758	Remote Similarity	NPD4694	Approved
0.5758	Remote Similarity	NPD5280	Approved
0.5755	Remote Similarity	NPD5926	Approved
0.5745	Remote Similarity	NPD3617	Approved
0.5743	Remote Similarity	NPD4753	Phase 2
0.5743	Remote Similarity	NPD5328	Approved
0.5727	Remote Similarity	NPD6675	Approved
0.5727	Remote Similarity	NPD5739	Approved
0.5727	Remote Similarity	NPD6402	Approved
0.5727	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4220	Pre-registration
0.5714	Remote Similarity	NPD4197	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6053	Discontinued
0.5701	Remote Similarity	NPD6404	Discontinued
0.57	Remote Similarity	NPD1282	Approved
0.5676	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5701	Approved
0.5673	Remote Similarity	NPD6001	Approved
0.5664	Remote Similarity	NPD7290	Approved
0.5664	Remote Similarity	NPD7102	Approved
0.5664	Remote Similarity	NPD6883	Approved
0.5657	Remote Similarity	NPD5363	Approved
0.5657	Remote Similarity	NPD6893	Approved
0.5657	Remote Similarity	NPD5329	Approved
0.5657	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4785	Approved
0.5652	Remote Similarity	NPD4784	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