NPASS Compound

Structure

NPC257618 OpenBabel07101718192D 27 28 0 0 0 0 0 0 0 0999 V2000 4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -2.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2429 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2429 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 0.2024 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 7.1449 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -1.7976 0.0000 C 0 0 0 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 10.6090 -1.2976 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 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 -0.2976 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 8.8769 -1.2976 0.0000 C 0 0 0 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 9.7429 -1.7976 0.0000 C 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 19 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 21 23 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.29
Volume:	428.241
LogP:	7.39
LogD:	5.54
LogS:	-4.848
# Rotatable Bonds:	9
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	3.351
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	1.841804441937711e-05
Pgp-inhibitor:	0.504
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.712
30% Bioavailability (F30%):	0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	93.94636535644531%
Volume Distribution (VD):	3.688
Pgp-substrate:	1.0284584760665894%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.299
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.503
CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.387
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	5.325
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.161
Skin Sensitization:	0.852
Carcinogencity:	0.033
Eye Corrosion:	0.047
Eye Irritation:	0.729
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC257618

Natural Product ID:	NPC257618
*Common Name:**	3-(4,8-Dimethyl-10-(2,6,6-Trimethylcyclohex-1-Enyl)Deca-3,7-Dienyl)Furan-2(5H)-One
IUPAC Name:	4-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethylcyclohexen-1-yl)deca-3,7-dienyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	JNEMQZQEAUFPOT-CWGBCDKESA-N
Standard InCHI:	InChI=1S/C25H38O2/c1-19(11-7-13-22-16-18-27-24(22)26)9-6-10-20(2)14-15-23-21(3)12-8-17-25(23,4)5/h10-11,16H,6-9,12-15,17-18H2,1-5H3/b19-11+,20-10+
SMILES:	C/C(=CCC/C(=C/CCC1=CCOC1=O)/C)/CCC1=C(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525915
PubChem CID:	10714247
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
NPO32964	hyrtios cf. erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869210]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	2.0	mm	PMID[565732]

☑ 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 NPC257618 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	174
0.1-0.2	1458
0.2-0.3	8217
0.3-0.4	17121
0.4-0.5	7956
0.5-0.6	5567
0.6-0.7	1957
0.7-0.8	218
0.8-0.85	21
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC27205
0.8784	High Similarity	NPC471299
0.8732	High Similarity	NPC222244
0.8732	High Similarity	NPC476489
0.8732	High Similarity	NPC476490
0.8732	High Similarity	NPC16349
0.8649	High Similarity	NPC471220
0.8462	Intermediate Similarity	NPC474865
0.8267	Intermediate Similarity	NPC473756
0.8267	Intermediate Similarity	NPC262747
0.8243	Intermediate Similarity	NPC228978
0.8228	Intermediate Similarity	NPC31086
0.8205	Intermediate Similarity	NPC200513
0.8194	Intermediate Similarity	NPC469660
0.8158	Intermediate Similarity	NPC474816
0.8158	Intermediate Similarity	NPC209135
0.8125	Intermediate Similarity	NPC474860
0.8125	Intermediate Similarity	NPC471300
0.8125	Intermediate Similarity	NPC189311
0.8116	Intermediate Similarity	NPC34883
0.8116	Intermediate Similarity	NPC226066
0.8108	Intermediate Similarity	NPC474758
0.8101	Intermediate Similarity	NPC193198
0.8028	Intermediate Similarity	NPC472266
0.8028	Intermediate Similarity	NPC203335
0.8026	Intermediate Similarity	NPC187568
0.8026	Intermediate Similarity	NPC41780
0.8	Intermediate Similarity	NPC475100
0.8	Intermediate Similarity	NPC149869
0.7971	Intermediate Similarity	NPC155849
0.7917	Intermediate Similarity	NPC276290
0.7901	Intermediate Similarity	NPC86316
0.7901	Intermediate Similarity	NPC65661
0.7901	Intermediate Similarity	NPC106416
0.7895	Intermediate Similarity	NPC4509
0.7875	Intermediate Similarity	NPC118423
0.7875	Intermediate Similarity	NPC22611
0.7875	Intermediate Similarity	NPC12283
0.7875	Intermediate Similarity	NPC474193
0.7867	Intermediate Similarity	NPC117746
0.7867	Intermediate Similarity	NPC294434
0.7867	Intermediate Similarity	NPC15499
0.7867	Intermediate Similarity	NPC259599
0.7857	Intermediate Similarity	NPC329698
0.7848	Intermediate Similarity	NPC475944
0.7831	Intermediate Similarity	NPC226863
0.7821	Intermediate Similarity	NPC150646
0.7808	Intermediate Similarity	NPC265574
0.7805	Intermediate Similarity	NPC211892
0.7792	Intermediate Similarity	NPC316500
0.7763	Intermediate Similarity	NPC329852
0.7763	Intermediate Similarity	NPC65650
0.775	Intermediate Similarity	NPC471298
0.775	Intermediate Similarity	NPC268122
0.775	Intermediate Similarity	NPC324170
0.775	Intermediate Similarity	NPC471296
0.775	Intermediate Similarity	NPC471218
0.775	Intermediate Similarity	NPC323251
0.775	Intermediate Similarity	NPC94200
0.7746	Intermediate Similarity	NPC470688
0.7738	Intermediate Similarity	NPC5509
0.7738	Intermediate Similarity	NPC174342
0.7733	Intermediate Similarity	NPC276336
0.7722	Intermediate Similarity	NPC268827
0.7711	Intermediate Similarity	NPC312561
0.7692	Intermediate Similarity	NPC128276
0.7692	Intermediate Similarity	NPC184737
0.7683	Intermediate Similarity	NPC30984
0.7681	Intermediate Similarity	NPC79756
0.7671	Intermediate Similarity	NPC218477
0.7671	Intermediate Similarity	NPC470256
0.7662	Intermediate Similarity	NPC40353
0.7662	Intermediate Similarity	NPC473223
0.7654	Intermediate Similarity	NPC472440
0.7654	Intermediate Similarity	NPC477124
0.7654	Intermediate Similarity	NPC474809
0.7654	Intermediate Similarity	NPC469
0.7654	Intermediate Similarity	NPC471297
0.7647	Intermediate Similarity	NPC471818
0.7639	Intermediate Similarity	NPC248125
0.7639	Intermediate Similarity	NPC185587
0.7632	Intermediate Similarity	NPC20025
0.7625	Intermediate Similarity	NPC471325
0.7612	Intermediate Similarity	NPC96663
0.76	Intermediate Similarity	NPC84038
0.7595	Intermediate Similarity	NPC469690
0.759	Intermediate Similarity	NPC168248
0.759	Intermediate Similarity	NPC220478
0.7586	Intermediate Similarity	NPC476596
0.7571	Intermediate Similarity	NPC151648
0.7564	Intermediate Similarity	NPC189206
0.7564	Intermediate Similarity	NPC57744
0.7564	Intermediate Similarity	NPC54996
0.7561	Intermediate Similarity	NPC30486
0.7561	Intermediate Similarity	NPC474359
0.7561	Intermediate Similarity	NPC471301
0.7561	Intermediate Similarity	NPC126518
0.7534	Intermediate Similarity	NPC194871
0.7532	Intermediate Similarity	NPC68624
0.7531	Intermediate Similarity	NPC186276
0.7531	Intermediate Similarity	NPC178676
0.7529	Intermediate Similarity	NPC251528
0.75	Intermediate Similarity	NPC474705
0.75	Intermediate Similarity	NPC195424
0.75	Intermediate Similarity	NPC182794
0.75	Intermediate Similarity	NPC475678
0.75	Intermediate Similarity	NPC476600
0.7471	Intermediate Similarity	NPC476597
0.7471	Intermediate Similarity	NPC475657
0.7471	Intermediate Similarity	NPC115021
0.7471	Intermediate Similarity	NPC476598
0.747	Intermediate Similarity	NPC163606
0.747	Intermediate Similarity	NPC472442
0.7468	Intermediate Similarity	NPC253749
0.7467	Intermediate Similarity	NPC67183
0.7467	Intermediate Similarity	NPC37929
0.7467	Intermediate Similarity	NPC64234
0.7465	Intermediate Similarity	NPC68110
0.7442	Intermediate Similarity	NPC159748
0.7442	Intermediate Similarity	NPC101651
0.7442	Intermediate Similarity	NPC232426
0.7442	Intermediate Similarity	NPC281942
0.7442	Intermediate Similarity	NPC51486
0.7439	Intermediate Similarity	NPC42476
0.7439	Intermediate Similarity	NPC475947
0.7436	Intermediate Similarity	NPC123360
0.7412	Intermediate Similarity	NPC472302
0.7407	Intermediate Similarity	NPC40228
0.7407	Intermediate Similarity	NPC282293
0.7407	Intermediate Similarity	NPC275507
0.7407	Intermediate Similarity	NPC14203
0.7407	Intermediate Similarity	NPC229584
0.7403	Intermediate Similarity	NPC476355
0.7403	Intermediate Similarity	NPC140287
0.7397	Intermediate Similarity	NPC116013
0.7381	Intermediate Similarity	NPC472863
0.7375	Intermediate Similarity	NPC178277
0.7375	Intermediate Similarity	NPC469620
0.7375	Intermediate Similarity	NPC190211
0.7368	Intermediate Similarity	NPC163003
0.7368	Intermediate Similarity	NPC181587
0.7368	Intermediate Similarity	NPC186531
0.7356	Intermediate Similarity	NPC65513
0.7356	Intermediate Similarity	NPC472814
0.7356	Intermediate Similarity	NPC477783
0.7356	Intermediate Similarity	NPC177037
0.7356	Intermediate Similarity	NPC473944
0.7356	Intermediate Similarity	NPC141831
0.7349	Intermediate Similarity	NPC471302
0.7349	Intermediate Similarity	NPC96055
0.7349	Intermediate Similarity	NPC318515
0.7349	Intermediate Similarity	NPC71626
0.7342	Intermediate Similarity	NPC473825
0.7333	Intermediate Similarity	NPC476059
0.7333	Intermediate Similarity	NPC232812
0.7333	Intermediate Similarity	NPC473603
0.7326	Intermediate Similarity	NPC284561
0.7326	Intermediate Similarity	NPC177141
0.7326	Intermediate Similarity	NPC168131
0.7317	Intermediate Similarity	NPC35556
0.7317	Intermediate Similarity	NPC173609
0.7308	Intermediate Similarity	NPC244166
0.7308	Intermediate Similarity	NPC469414
0.7308	Intermediate Similarity	NPC329826
0.7297	Intermediate Similarity	NPC254886
0.7297	Intermediate Similarity	NPC21998
0.7273	Intermediate Similarity	NPC287878
0.7273	Intermediate Similarity	NPC144947
0.7273	Intermediate Similarity	NPC139692
0.7273	Intermediate Similarity	NPC135703
0.7262	Intermediate Similarity	NPC110405
0.7262	Intermediate Similarity	NPC155873
0.7262	Intermediate Similarity	NPC473251
0.7262	Intermediate Similarity	NPC42586
0.7262	Intermediate Similarity	NPC217394
0.7262	Intermediate Similarity	NPC177932
0.7262	Intermediate Similarity	NPC474013
0.725	Intermediate Similarity	NPC105197
0.725	Intermediate Similarity	NPC299235
0.7241	Intermediate Similarity	NPC477782
0.7241	Intermediate Similarity	NPC469595
0.7241	Intermediate Similarity	NPC8062
0.7241	Intermediate Similarity	NPC212679
0.7241	Intermediate Similarity	NPC220454
0.7241	Intermediate Similarity	NPC273199
0.7229	Intermediate Similarity	NPC16488
0.7229	Intermediate Similarity	NPC474976
0.7229	Intermediate Similarity	NPC311070
0.7229	Intermediate Similarity	NPC30502
0.7229	Intermediate Similarity	NPC472377
0.7229	Intermediate Similarity	NPC474790
0.7222	Intermediate Similarity	NPC179087
0.7222	Intermediate Similarity	NPC217940
0.7222	Intermediate Similarity	NPC29952
0.7222	Intermediate Similarity	NPC325960
0.7222	Intermediate Similarity	NPC210303
0.7222	Intermediate Similarity	NPC44343
0.7222	Intermediate Similarity	NPC319692
0.7222	Intermediate Similarity	NPC474658
0.7215	Intermediate Similarity	NPC19907

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 NPC257618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1964
0.2-0.3	4421
0.3-0.4	1888
0.4-0.5	469
0.5-0.6	216
0.6-0.7	23
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8243	Intermediate Similarity	NPD8039	Approved
0.8205	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5209	Approved
0.7262	Intermediate Similarity	NPD1694	Approved
0.7121	Intermediate Similarity	NPD6927	Phase 3
0.7083	Intermediate Similarity	NPD4191	Approved
0.7083	Intermediate Similarity	NPD4192	Approved
0.7083	Intermediate Similarity	NPD4194	Approved
0.7083	Intermediate Similarity	NPD4193	Approved
0.6977	Remote Similarity	NPD7146	Approved
0.6977	Remote Similarity	NPD5330	Approved
0.6977	Remote Similarity	NPD6684	Approved
0.6977	Remote Similarity	NPD7521	Approved
0.6977	Remote Similarity	NPD6409	Approved
0.6977	Remote Similarity	NPD7334	Approved
0.6818	Remote Similarity	NPD5737	Approved
0.6818	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6672	Approved
0.6702	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD7640	Approved
0.6632	Remote Similarity	NPD7639	Approved
0.6593	Remote Similarity	NPD5693	Phase 1
0.6556	Remote Similarity	NPD6051	Approved
0.6526	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD6686	Approved
0.6484	Remote Similarity	NPD46	Approved
0.6484	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5343	Approved
0.6375	Remote Similarity	NPD4691	Approved
0.6374	Remote Similarity	NPD6080	Approved
0.6374	Remote Similarity	NPD6904	Approved
0.6374	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD3573	Approved
0.6292	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7331	Phase 2
0.6279	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7748	Approved
0.6277	Remote Similarity	NPD7900	Approved
0.6264	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD4137	Phase 3
0.6237	Remote Similarity	NPD6050	Approved
0.6237	Remote Similarity	NPD7637	Suspended
0.6222	Remote Similarity	NPD6098	Approved
0.6211	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5695	Phase 3
0.6173	Remote Similarity	NPD4747	Approved
0.617	Remote Similarity	NPD6399	Phase 3
0.6164	Remote Similarity	NPD4219	Approved
0.6145	Remote Similarity	NPD5733	Approved
0.6145	Remote Similarity	NPD4058	Approved
0.6129	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD5692	Phase 3
0.6129	Remote Similarity	NPD5207	Approved
0.6118	Remote Similarity	NPD4756	Discovery
0.6111	Remote Similarity	NPD1696	Phase 3
0.6111	Remote Similarity	NPD5363	Approved
0.6098	Remote Similarity	NPD5276	Approved
0.6092	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7902	Approved
0.6076	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5362	Discontinued
0.6064	Remote Similarity	NPD5694	Approved
0.6064	Remote Similarity	NPD6411	Approved
0.6064	Remote Similarity	NPD7515	Phase 2
0.6022	Remote Similarity	NPD1695	Approved
0.602	Remote Similarity	NPD5696	Approved
0.602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD287	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.597	Remote Similarity	NPD6097	Approved
0.597	Remote Similarity	NPD6096	Approved
0.596	Remote Similarity	NPD6404	Discontinued
0.5952	Remote Similarity	NPD4687	Approved
0.5938	Remote Similarity	NPD6001	Approved
0.5922	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD29	Approved
0.5915	Remote Similarity	NPD28	Approved
0.5909	Remote Similarity	NPD4822	Approved
0.5909	Remote Similarity	NPD4820	Approved
0.5909	Remote Similarity	NPD4819	Approved
0.5909	Remote Similarity	NPD4695	Discontinued
0.5909	Remote Similarity	NPD4821	Approved
0.5905	Remote Similarity	NPD6371	Approved
0.5895	Remote Similarity	NPD6079	Approved
0.5889	Remote Similarity	NPD5332	Approved
0.5889	Remote Similarity	NPD5331	Approved
0.5882	Remote Similarity	NPD1452	Discontinued
0.587	Remote Similarity	NPD4519	Discontinued
0.587	Remote Similarity	NPD4623	Approved
0.587	Remote Similarity	NPD3618	Phase 1
0.587	Remote Similarity	NPD5279	Phase 3
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5862	Remote Similarity	NPD4268	Approved
0.5862	Remote Similarity	NPD4271	Approved
0.5851	Remote Similarity	NPD5328	Approved
0.5851	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6101	Approved
0.5844	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4790	Discontinued
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5824	Remote Similarity	NPD4786	Approved
0.5816	Remote Similarity	NPD7732	Phase 3
0.581	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6648	Approved
0.5794	Remote Similarity	NPD6053	Discontinued
0.5778	Remote Similarity	NPD4221	Approved
0.5778	Remote Similarity	NPD4270	Approved
0.5778	Remote Similarity	NPD4223	Phase 3
0.5778	Remote Similarity	NPD4269	Approved
0.5778	Remote Similarity	NPD6435	Approved
0.5778	Remote Similarity	NPD3667	Approved
0.5769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5697	Approved
0.5761	Remote Similarity	NPD5329	Approved
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.575	Remote Similarity	NPD7341	Phase 2
0.5743	Remote Similarity	NPD5344	Discontinued
0.5732	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4252	Approved
0.5729	Remote Similarity	NPD5281	Approved
0.5729	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD5654	Approved
0.5701	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD6649	Approved
0.5701	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5699	Remote Similarity	NPD5786	Approved
0.5699	Remote Similarity	NPD5690	Phase 2
0.5698	Remote Similarity	NPD8264	Approved
0.5684	Remote Similarity	NPD4753	Phase 2
0.5684	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3196	Approved
0.5676	Remote Similarity	NPD3195	Phase 2
0.5676	Remote Similarity	NPD4266	Approved
0.5676	Remote Similarity	NPD3194	Approved
0.5673	Remote Similarity	NPD6008	Approved
0.5667	Remote Similarity	NPD5369	Approved
0.566	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6013	Approved
0.566	Remote Similarity	NPD6373	Approved
0.566	Remote Similarity	NPD6012	Approved
0.5658	Remote Similarity	NPD8779	Phase 3
0.5652	Remote Similarity	NPD3668	Phase 3
0.5652	Remote Similarity	NPD4197	Approved
0.5652	Remote Similarity	NPD3174	Discontinued
0.5648	Remote Similarity	NPD8297	Approved
0.5648	Remote Similarity	NPD6882	Approved
0.5638	Remote Similarity	NPD4250	Approved
0.5638	Remote Similarity	NPD4251	Approved
0.5631	Remote Similarity	NPD6647	Phase 2
0.5631	Remote Similarity	NPD6052	Approved
0.5619	Remote Similarity	NPD6614	Approved
0.5619	Remote Similarity	NPD5701	Approved
0.5618	Remote Similarity	NPD4195	Approved
0.5607	Remote Similarity	NPD2067	Discontinued
0.56	Remote Similarity	NPD5959	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