NPASS Compound

Structure

NPC471297 OpenBabel07101718292D 29 30 0 0 1 0 0 0 0 0999 V2000 3.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4282 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -6.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 17 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	445.822
LogP:	5.409
LogD:	4.578
LogS:	-3.568
# Rotatable Bonds:	9
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.097
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:	-5.148
MDCK Permeability:	2.4299626602442004e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.839
Human Intestinal Absorption (HIA):	0.346
20% Bioavailability (F20%):	0.65
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	94.35940551757812%
Volume Distribution (VD):	1.52
Pgp-substrate:	1.102550983428955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.397
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	4.802
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.681
Skin Sensitization:	0.699
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.188
Respiratory Toxicity:	0.277

Download Data

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

Natural Product: NPC471297

Natural Product ID:	NPC471297
*Common Name:**	16-Hydroxyluffariellolide
IUPAC Name:	2-hydroxy-3-[(3E,7E)-10-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-4,8-dimethyldeca-3,7-dienyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	HIRZCXOPFLDJON-SCNFBCNRSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-17(10-7-11-20-16-23(27)29-24(20)28)8-6-9-18(2)12-13-21-19(3)22(26)14-15-25(21,4)5/h9-10,16,22,24,26,28H,6-8,11-15H2,1-5H3/b17-10+,18-9+
SMILES:	CC1=C(C(CCC1O)(C)C)CCC(=CCCC(=CCCC2=CC(=O)OC2O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409154
PubChem CID:	21778236
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
NPO33221	hyrtios communis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944963]

☑ 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
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[497461]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	10000.0	nM	PMID[497461]

☑ 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 NPC471297 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	170
0.1-0.2	1243
0.2-0.3	5497
0.3-0.4	15766
0.4-0.5	9181
0.5-0.6	7207
0.6-0.7	3209
0.7-0.8	376
0.8-0.85	24
0.85-0.9	16
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC471298
0.9375	High Similarity	NPC471301
0.9375	High Similarity	NPC471302
0.9367	High Similarity	NPC323251
0.9241	High Similarity	NPC475944
0.9221	High Similarity	NPC473756
0.9136	High Similarity	NPC126518
0.9024	High Similarity	NPC163606
0.8889	High Similarity	NPC324170
0.8861	High Similarity	NPC474816
0.8861	High Similarity	NPC209135
0.8824	High Similarity	NPC470734
0.8795	High Similarity	NPC471300
0.8795	High Similarity	NPC474860
0.878	High Similarity	NPC474809
0.8734	High Similarity	NPC262747
0.8706	High Similarity	NPC472810
0.8706	High Similarity	NPC472809
0.8636	High Similarity	NPC298973
0.8636	High Similarity	NPC104925
0.8621	High Similarity	NPC472811
0.8571	High Similarity	NPC42586
0.8571	High Similarity	NPC473251
0.8523	High Similarity	NPC472812
0.8488	Intermediate Similarity	NPC474629
0.8488	Intermediate Similarity	NPC472378
0.8462	Intermediate Similarity	NPC476489
0.8462	Intermediate Similarity	NPC476490
0.8434	Intermediate Similarity	NPC471296
0.8427	Intermediate Similarity	NPC469697
0.8409	Intermediate Similarity	NPC477122
0.8333	Intermediate Similarity	NPC472441
0.8295	Intermediate Similarity	NPC281942
0.8295	Intermediate Similarity	NPC232426
0.8242	Intermediate Similarity	NPC162346
0.8235	Intermediate Similarity	NPC31086
0.8235	Intermediate Similarity	NPC474865
0.8228	Intermediate Similarity	NPC222244
0.8228	Intermediate Similarity	NPC16349
0.8222	Intermediate Similarity	NPC470255
0.8202	Intermediate Similarity	NPC329842
0.8202	Intermediate Similarity	NPC141831
0.8172	Intermediate Similarity	NPC324841
0.8152	Intermediate Similarity	NPC477719
0.8152	Intermediate Similarity	NPC477718
0.814	Intermediate Similarity	NPC472442
0.8118	Intermediate Similarity	NPC311070
0.8118	Intermediate Similarity	NPC472440
0.8118	Intermediate Similarity	NPC472377
0.809	Intermediate Similarity	NPC477782
0.809	Intermediate Similarity	NPC78973
0.8046	Intermediate Similarity	NPC211892
0.8046	Intermediate Similarity	NPC131813
0.8022	Intermediate Similarity	NPC474554
0.8022	Intermediate Similarity	NPC324078
0.8	Intermediate Similarity	NPC477783
0.7979	Intermediate Similarity	NPC477721
0.7979	Intermediate Similarity	NPC477716
0.7975	Intermediate Similarity	NPC4299
0.7957	Intermediate Similarity	NPC475709
0.7955	Intermediate Similarity	NPC312561
0.7935	Intermediate Similarity	NPC476487
0.7935	Intermediate Similarity	NPC476488
0.7927	Intermediate Similarity	NPC477202
0.7912	Intermediate Similarity	NPC53555
0.7907	Intermediate Similarity	NPC42476
0.7895	Intermediate Similarity	NPC477717
0.7872	Intermediate Similarity	NPC473154
0.7872	Intermediate Similarity	NPC474440
0.7857	Intermediate Similarity	NPC242767
0.7849	Intermediate Similarity	NPC240673
0.7849	Intermediate Similarity	NPC17578
0.7849	Intermediate Similarity	NPC165632
0.7848	Intermediate Similarity	NPC101622
0.7831	Intermediate Similarity	NPC477203
0.7826	Intermediate Similarity	NPC475572
0.7826	Intermediate Similarity	NPC474555
0.7821	Intermediate Similarity	NPC472266
0.7816	Intermediate Similarity	NPC470800
0.7812	Intermediate Similarity	NPC472815
0.7791	Intermediate Similarity	NPC471218
0.7791	Intermediate Similarity	NPC256112
0.7778	Intermediate Similarity	NPC251528
0.7766	Intermediate Similarity	NPC98112
0.7766	Intermediate Similarity	NPC53844
0.7755	Intermediate Similarity	NPC153095
0.7753	Intermediate Similarity	NPC475678
0.775	Intermediate Similarity	NPC469660
0.7742	Intermediate Similarity	NPC13924
0.7727	Intermediate Similarity	NPC471494
0.7727	Intermediate Similarity	NPC473659
0.7727	Intermediate Similarity	NPC471795
0.7727	Intermediate Similarity	NPC329630
0.7727	Intermediate Similarity	NPC474694
0.7727	Intermediate Similarity	NPC475860
0.7727	Intermediate Similarity	NPC35933
0.7711	Intermediate Similarity	NPC469880
0.7708	Intermediate Similarity	NPC471075
0.7701	Intermediate Similarity	NPC12283
0.7701	Intermediate Similarity	NPC474193
0.7692	Intermediate Similarity	NPC469403
0.7692	Intermediate Similarity	NPC221111
0.7692	Intermediate Similarity	NPC280149
0.7674	Intermediate Similarity	NPC170303
0.766	Intermediate Similarity	NPC470801
0.7654	Intermediate Similarity	NPC257618
0.7647	Intermediate Similarity	NPC471299
0.764	Intermediate Similarity	NPC311163
0.764	Intermediate Similarity	NPC474062
0.7634	Intermediate Similarity	NPC105490
0.7629	Intermediate Similarity	NPC201191
0.7619	Intermediate Similarity	NPC315394
0.7614	Intermediate Similarity	NPC186155
0.7614	Intermediate Similarity	NPC78673
0.7614	Intermediate Similarity	NPC474693
0.7614	Intermediate Similarity	NPC160517
0.7614	Intermediate Similarity	NPC475706
0.7604	Intermediate Similarity	NPC477720
0.7604	Intermediate Similarity	NPC477972
0.7604	Intermediate Similarity	NPC20113
0.7604	Intermediate Similarity	NPC161527
0.7604	Intermediate Similarity	NPC477968
0.7604	Intermediate Similarity	NPC228251
0.7604	Intermediate Similarity	NPC477971
0.7604	Intermediate Similarity	NPC219285
0.76	Intermediate Similarity	NPC470024
0.76	Intermediate Similarity	NPC38948
0.7586	Intermediate Similarity	NPC122945
0.7586	Intermediate Similarity	NPC109938
0.7582	Intermediate Similarity	NPC5509
0.7576	Intermediate Similarity	NPC172867
0.7561	Intermediate Similarity	NPC477085
0.7558	Intermediate Similarity	NPC206062
0.7558	Intermediate Similarity	NPC10636
0.7558	Intermediate Similarity	NPC281880
0.7556	Intermediate Similarity	NPC166857
0.7556	Intermediate Similarity	NPC471796
0.7556	Intermediate Similarity	NPC313658
0.7556	Intermediate Similarity	NPC45409
0.7556	Intermediate Similarity	NPC316138
0.7553	Intermediate Similarity	NPC276110
0.7551	Intermediate Similarity	NPC120009
0.7529	Intermediate Similarity	NPC326753
0.7529	Intermediate Similarity	NPC471220
0.7529	Intermediate Similarity	NPC184737
0.7528	Intermediate Similarity	NPC474013
0.7528	Intermediate Similarity	NPC11804
0.7528	Intermediate Similarity	NPC30984
0.7527	Intermediate Similarity	NPC115021
0.7527	Intermediate Similarity	NPC238090
0.7527	Intermediate Similarity	NPC472640
0.7527	Intermediate Similarity	NPC242069
0.7527	Intermediate Similarity	NPC156553
0.7527	Intermediate Similarity	NPC205034
0.7527	Intermediate Similarity	NPC472195
0.7527	Intermediate Similarity	NPC152778
0.7527	Intermediate Similarity	NPC162615
0.7527	Intermediate Similarity	NPC139692
0.7527	Intermediate Similarity	NPC7349
0.7527	Intermediate Similarity	NPC472196
0.7527	Intermediate Similarity	NPC472641
0.7526	Intermediate Similarity	NPC198992
0.7525	Intermediate Similarity	NPC206618
0.75	Intermediate Similarity	NPC202886
0.75	Intermediate Similarity	NPC475074
0.75	Intermediate Similarity	NPC161045
0.75	Intermediate Similarity	NPC325229
0.75	Intermediate Similarity	NPC275086
0.75	Intermediate Similarity	NPC476927
0.75	Intermediate Similarity	NPC477124
0.75	Intermediate Similarity	NPC27205
0.75	Intermediate Similarity	NPC23748
0.75	Intermediate Similarity	NPC470817
0.75	Intermediate Similarity	NPC109376
0.75	Intermediate Similarity	NPC310479
0.75	Intermediate Similarity	NPC472642
0.75	Intermediate Similarity	NPC182136
0.7474	Intermediate Similarity	NPC16967
0.7474	Intermediate Similarity	NPC242848
0.7474	Intermediate Similarity	NPC234993
0.7474	Intermediate Similarity	NPC190713
0.7474	Intermediate Similarity	NPC473153
0.7474	Intermediate Similarity	NPC134072
0.7471	Intermediate Similarity	NPC112868
0.7471	Intermediate Similarity	NPC159148
0.7449	Intermediate Similarity	NPC121423
0.7449	Intermediate Similarity	NPC238397
0.7449	Intermediate Similarity	NPC471363
0.7447	Intermediate Similarity	NPC159698
0.7447	Intermediate Similarity	NPC57117
0.7447	Intermediate Similarity	NPC477722
0.7447	Intermediate Similarity	NPC53685
0.7444	Intermediate Similarity	NPC61527
0.7444	Intermediate Similarity	NPC471219
0.7442	Intermediate Similarity	NPC321728
0.7442	Intermediate Similarity	NPC139712
0.7439	Intermediate Similarity	NPC477086
0.7439	Intermediate Similarity	NPC472254
0.7439	Intermediate Similarity	NPC477087
0.7426	Intermediate Similarity	NPC224660

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 NPC471297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1763
0.2-0.3	3987
0.3-0.4	2411
0.4-0.5	518
0.5-0.6	279
0.6-0.7	49
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9136	High Similarity	NPD6400	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6686	Approved
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD5785	Approved
0.6818	Remote Similarity	NPD7328	Approved
0.6818	Remote Similarity	NPD7327	Approved
0.68	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD46	Approved
0.6757	Remote Similarity	NPD7516	Approved
0.675	Remote Similarity	NPD4192	Approved
0.675	Remote Similarity	NPD4193	Approved
0.675	Remote Similarity	NPD4191	Approved
0.675	Remote Similarity	NPD4194	Approved
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7154	Phase 3
0.6701	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6051	Approved
0.6637	Remote Similarity	NPD7503	Approved
0.6637	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD8335	Approved
0.6637	Remote Similarity	NPD8380	Approved
0.6637	Remote Similarity	NPD8296	Approved
0.6637	Remote Similarity	NPD8379	Approved
0.6637	Remote Similarity	NPD8033	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7748	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6531	Remote Similarity	NPD7515	Phase 2
0.6465	Remote Similarity	NPD5778	Approved
0.6465	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6421	Remote Similarity	NPD5363	Approved
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD4821	Approved
0.641	Remote Similarity	NPD7507	Approved
0.6408	Remote Similarity	NPD6648	Approved
0.6404	Remote Similarity	NPD8264	Approved
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6383	Remote Similarity	NPD6695	Phase 3
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD4271	Approved
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6355	Remote Similarity	NPD6412	Phase 2
0.6354	Remote Similarity	NPD7334	Approved
0.6354	Remote Similarity	NPD6409	Approved
0.6354	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD6684	Approved
0.6354	Remote Similarity	NPD7521	Approved
0.6354	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.6341	Remote Similarity	NPD368	Approved
0.6337	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6399	Phase 3
0.6277	Remote Similarity	NPD4269	Approved
0.6277	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD7839	Suspended
0.6275	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6903	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6224	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6882	Approved
0.6196	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD5786	Approved
0.6182	Remote Similarity	NPD6371	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6162	Remote Similarity	NPD6101	Approved
0.6162	Remote Similarity	NPD5328	Approved
0.6162	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7320	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6146	Remote Similarity	NPD3665	Phase 1
0.6146	Remote Similarity	NPD3133	Approved
0.6146	Remote Similarity	NPD3666	Approved
0.6129	Remote Similarity	NPD7645	Phase 2
0.6129	Remote Similarity	NPD6929	Approved
0.6125	Remote Similarity	NPD4219	Approved
0.6122	Remote Similarity	NPD7750	Discontinued
0.6122	Remote Similarity	NPD7524	Approved
0.6122	Remote Similarity	NPD4250	Approved
0.6122	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6111	Remote Similarity	NPD4211	Phase 1
0.6105	Remote Similarity	NPD6435	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6087	Remote Similarity	NPD6925	Approved
0.6087	Remote Similarity	NPD4756	Discovery
0.6087	Remote Similarity	NPD5776	Phase 2
0.6082	Remote Similarity	NPD1696	Phase 3
0.6078	Remote Similarity	NPD7900	Approved
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6053	Discontinued
0.6068	Remote Similarity	NPD8513	Phase 3
0.6068	Remote Similarity	NPD8515	Approved
0.6068	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD8516	Approved
0.6064	Remote Similarity	NPD7332	Phase 2
0.6064	Remote Similarity	NPD6930	Phase 2
0.6064	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD6931	Approved
0.6064	Remote Similarity	NPD4252	Approved
0.6064	Remote Similarity	NPD7514	Phase 3
0.6055	Remote Similarity	NPD5697	Approved
0.6055	Remote Similarity	NPD5701	Approved
0.6047	Remote Similarity	NPD7331	Phase 2
0.6044	Remote Similarity	NPD6942	Approved
0.6044	Remote Similarity	NPD7339	Approved
0.604	Remote Similarity	NPD6079	Approved
0.604	Remote Similarity	NPD7983	Approved
0.604	Remote Similarity	NPD5693	Phase 1
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7290	Approved
0.6036	Remote Similarity	NPD7102	Approved
0.6024	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6923	Approved
0.6023	Remote Similarity	NPD6922	Approved
0.6022	Remote Similarity	NPD7145	Approved
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6902	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5982	Remote Similarity	NPD6869	Approved
0.5979	Remote Similarity	NPD4786	Approved
0.5978	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6933	Approved
0.5955	Remote Similarity	NPD7144	Approved
0.5955	Remote Similarity	NPD7143	Approved
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6014	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5926	Remote Similarity	NPD6647	Phase 2
0.5895	Remote Similarity	NPD5368	Approved
0.5889	Remote Similarity	NPD7152	Approved
0.5889	Remote Similarity	NPD7151	Approved
0.5889	Remote Similarity	NPD7150	Approved
0.5882	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7087	Discontinued
0.5876	Remote Similarity	NPD6110	Phase 1
0.5865	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7505	Discontinued
0.5859	Remote Similarity	NPD4519	Discontinued
0.5859	Remote Similarity	NPD4623	Approved
0.5842	Remote Similarity	NPD4753	Phase 2
0.5842	Remote Similarity	NPD6673	Approved
0.5842	Remote Similarity	NPD6080	Approved
0.5842	Remote Similarity	NPD5370	Suspended
0.5842	Remote Similarity	NPD689	Discontinued
0.5842	Remote Similarity	NPD6904	Approved
0.5841	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8328	Phase 3
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD6898	Phase 1
0.5825	Remote Similarity	NPD4202	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