NPASS Compound

Structure

NPC329630 OpenBabel07101719252D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.9960 -0.6918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6258 1.5318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7598 -2.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0243 -2.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6258 0.5318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5817 -2.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 1.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5477 -2.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8937 1.5318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3229 -1.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 0.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2207 -1.9165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6258 -1.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9278 -1.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6258 -0.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5799 -1.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -1.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7598 1.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7598 -1.9682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3570 -0.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8937 -0.4682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9986 0.0523 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.8937 -1.4682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7598 0.0318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1924 -1.3243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5433 0.8910 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 2 0 0 0 0 3 19 1 0 0 0 0 6 8 1 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 18 25 1 0 0 0 0 19 24 1 1 0 0 0 20 23 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.27
Volume:	428.475
LogP:	5.725
LogD:	4.662
LogS:	-4.558
# Rotatable Bonds:	5
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	4.725
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:	-4.817
MDCK Permeability:	2.4757691790000536e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	97.83110046386719%
Volume Distribution (VD):	2.324
Pgp-substrate:	3.5502359867095947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	5.692
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.95
Carcinogencity:	0.797
Eye Corrosion:	0.028
Eye Irritation:	0.594
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC329630

Natural Product ID:	NPC329630
*Common Name:**	Palauolide
IUPAC Name:	3-[(1E,3E)-6-[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-4-methylhexa-1,3-dienyl]-2-hydroxy-2H-furan-5-one
Synonyms:	Palauolide
Standard InCHIKey:	JFXRRRSBGSPRCO-MMWFQGMQSA-N
Standard InCHI:	InChI=1S/C25H36O3/c1-17(8-6-10-20-16-22(26)28-23(20)27)12-14-24(4)19(3)13-15-25(5)18(2)9-7-11-21(24)25/h6,8,10,16,19,21,23,27H,2,7,9,11-15H2,1,3-5H3/b10-6+,17-8+/t19-,21-,23?,24+,25+/m0/s1
SMILES:	CC1CCC2(C(C1(C)CCC(=CC=CC3=CC(=O)OC3O)C)CCCC2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465035
PubChem CID:	13859138
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
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374971]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975486]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]

☑ 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	12

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	=	7.7	ug.mL-1	PMID[569918]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	30.0	ug.mL-1	PMID[569918]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	37.0	ug.mL-1	PMID[569918]
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	51.2	ug.mL-1	PMID[569918]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	30.0	ug.mL-1	PMID[569918]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10.1	ug.mL-1	PMID[569918]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	43.5	ug.mL-1	PMID[569918]
NPT386	Cell Line	KM12	Homo sapiens	IC50	=	14.4	ug.mL-1	PMID[569918]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	23.6	ug.mL-1	PMID[569918]
NPT383	Cell Line	SNB-19	Homo sapiens	IC50	=	52.1	ug.mL-1	PMID[569918]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[569918]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	53.0	ug.mL-1	PMID[569918]

☑ 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 NPC329630 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	155
0.1-0.2	1152
0.2-0.3	5355
0.3-0.4	15130
0.4-0.5	10382
0.5-0.6	7907
0.6-0.7	2278
0.7-0.8	303
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC470800
0.8941	High Similarity	NPC474629
0.875	High Similarity	NPC242069
0.8675	High Similarity	NPC324170
0.8652	High Similarity	NPC470255
0.8588	High Similarity	NPC42586
0.8588	High Similarity	NPC473251
0.8587	High Similarity	NPC477720
0.8571	High Similarity	NPC42476
0.8539	High Similarity	NPC469939
0.8444	Intermediate Similarity	NPC469697
0.8395	Intermediate Similarity	NPC4509
0.8372	Intermediate Similarity	NPC217394
0.8295	Intermediate Similarity	NPC472810
0.8295	Intermediate Similarity	NPC472809
0.8293	Intermediate Similarity	NPC473756
0.8276	Intermediate Similarity	NPC211892
0.8261	Intermediate Similarity	NPC162346
0.8242	Intermediate Similarity	NPC298973
0.8242	Intermediate Similarity	NPC324078
0.8242	Intermediate Similarity	NPC104925
0.8235	Intermediate Similarity	NPC16321
0.8222	Intermediate Similarity	NPC472811
0.8222	Intermediate Similarity	NPC477122
0.8202	Intermediate Similarity	NPC470734
0.8132	Intermediate Similarity	NPC472812
0.8111	Intermediate Similarity	NPC477782
0.8111	Intermediate Similarity	NPC182136
0.809	Intermediate Similarity	NPC196407
0.8085	Intermediate Similarity	NPC474440
0.8046	Intermediate Similarity	NPC471302
0.8046	Intermediate Similarity	NPC126518
0.8023	Intermediate Similarity	NPC323251
0.8022	Intermediate Similarity	NPC477783
0.8	Intermediate Similarity	NPC251528
0.7979	Intermediate Similarity	NPC477719
0.7979	Intermediate Similarity	NPC98112
0.7979	Intermediate Similarity	NPC477718
0.7957	Intermediate Similarity	NPC472441
0.7955	Intermediate Similarity	NPC163606
0.7931	Intermediate Similarity	NPC469
0.7931	Intermediate Similarity	NPC311070
0.7931	Intermediate Similarity	NPC472440
0.7912	Intermediate Similarity	NPC78973
0.7912	Intermediate Similarity	NPC310479
0.7841	Intermediate Similarity	NPC471301
0.7826	Intermediate Similarity	NPC329842
0.7816	Intermediate Similarity	NPC268122
0.7816	Intermediate Similarity	NPC94200
0.7816	Intermediate Similarity	NPC471298
0.7812	Intermediate Similarity	NPC477716
0.7812	Intermediate Similarity	NPC477721
0.7812	Intermediate Similarity	NPC324841
0.7753	Intermediate Similarity	NPC472442
0.7753	Intermediate Similarity	NPC471795
0.7742	Intermediate Similarity	NPC205034
0.7742	Intermediate Similarity	NPC162615
0.7742	Intermediate Similarity	NPC152778
0.7732	Intermediate Similarity	NPC477717
0.7727	Intermediate Similarity	NPC118423
0.7727	Intermediate Similarity	NPC471297
0.7722	Intermediate Similarity	NPC185587
0.7717	Intermediate Similarity	NPC221111
0.7717	Intermediate Similarity	NPC280149
0.7717	Intermediate Similarity	NPC469403
0.7684	Intermediate Similarity	NPC16967
0.7684	Intermediate Similarity	NPC473153
0.7667	Intermediate Similarity	NPC474062
0.7647	Intermediate Similarity	NPC262747
0.7624	Intermediate Similarity	NPC470024
0.7609	Intermediate Similarity	NPC174342
0.7604	Intermediate Similarity	NPC475709
0.7604	Intermediate Similarity	NPC208094
0.76	Intermediate Similarity	NPC218158
0.76	Intermediate Similarity	NPC172867
0.7595	Intermediate Similarity	NPC107258
0.759	Intermediate Similarity	NPC476490
0.759	Intermediate Similarity	NPC476489
0.7582	Intermediate Similarity	NPC475678
0.7579	Intermediate Similarity	NPC209355
0.7576	Intermediate Similarity	NPC45897
0.7558	Intermediate Similarity	NPC474816
0.7558	Intermediate Similarity	NPC209135
0.7556	Intermediate Similarity	NPC30984
0.7556	Intermediate Similarity	NPC106416
0.7556	Intermediate Similarity	NPC474860
0.7556	Intermediate Similarity	NPC471300
0.7556	Intermediate Similarity	NPC86316
0.7553	Intermediate Similarity	NPC166346
0.7553	Intermediate Similarity	NPC53555
0.7551	Intermediate Similarity	NPC63249
0.7527	Intermediate Similarity	NPC281942
0.7527	Intermediate Similarity	NPC232426
0.7526	Intermediate Similarity	NPC473154
0.7525	Intermediate Similarity	NPC475074
0.7525	Intermediate Similarity	NPC109376
0.75	Intermediate Similarity	NPC470801
0.75	Intermediate Similarity	NPC259156
0.75	Intermediate Similarity	NPC472378
0.75	Intermediate Similarity	NPC242945
0.7475	Intermediate Similarity	NPC134077
0.7475	Intermediate Similarity	NPC472815
0.7474	Intermediate Similarity	NPC191521
0.7473	Intermediate Similarity	NPC471219
0.7473	Intermediate Similarity	NPC118266
0.7473	Intermediate Similarity	NPC131813
0.7473	Intermediate Similarity	NPC173917
0.7473	Intermediate Similarity	NPC168248
0.7471	Intermediate Similarity	NPC17550
0.7471	Intermediate Similarity	NPC242767
0.7468	Intermediate Similarity	NPC329698
0.7451	Intermediate Similarity	NPC38948
0.7451	Intermediate Similarity	NPC224660
0.7447	Intermediate Similarity	NPC141831
0.7419	Intermediate Similarity	NPC474396
0.7419	Intermediate Similarity	NPC474844
0.7419	Intermediate Similarity	NPC50488
0.7419	Intermediate Similarity	NPC471654
0.7419	Intermediate Similarity	NPC79027
0.7416	Intermediate Similarity	NPC471296
0.7416	Intermediate Similarity	NPC471218
0.7404	Intermediate Similarity	NPC17791
0.74	Intermediate Similarity	NPC120009
0.74	Intermediate Similarity	NPC134270
0.7396	Intermediate Similarity	NPC13924
0.7396	Intermediate Similarity	NPC276110
0.7396	Intermediate Similarity	NPC295347
0.7391	Intermediate Similarity	NPC312561
0.7391	Intermediate Similarity	NPC471796
0.7386	Intermediate Similarity	NPC10636
0.7379	Intermediate Similarity	NPC206618
0.7368	Intermediate Similarity	NPC472303
0.7363	Intermediate Similarity	NPC475860
0.7363	Intermediate Similarity	NPC474694
0.7363	Intermediate Similarity	NPC109528
0.7363	Intermediate Similarity	NPC65661
0.7363	Intermediate Similarity	NPC473659
0.7356	Intermediate Similarity	NPC105197
0.7347	Intermediate Similarity	NPC278673
0.734	Intermediate Similarity	NPC253186
0.7333	Intermediate Similarity	NPC279639
0.7333	Intermediate Similarity	NPC476927
0.7333	Intermediate Similarity	NPC477124
0.7333	Intermediate Similarity	NPC321272
0.7333	Intermediate Similarity	NPC3856
0.7333	Intermediate Similarity	NPC328074
0.7333	Intermediate Similarity	NPC317460
0.7333	Intermediate Similarity	NPC474790
0.7333	Intermediate Similarity	NPC474809
0.7333	Intermediate Similarity	NPC472377
0.7333	Intermediate Similarity	NPC23748
0.7333	Intermediate Similarity	NPC470025
0.7333	Intermediate Similarity	NPC474976
0.7327	Intermediate Similarity	NPC470321
0.7327	Intermediate Similarity	NPC473207
0.7327	Intermediate Similarity	NPC201880
0.7327	Intermediate Similarity	NPC264867
0.7327	Intermediate Similarity	NPC81567
0.7308	Intermediate Similarity	NPC316708
0.7303	Intermediate Similarity	NPC159148
0.7303	Intermediate Similarity	NPC475944
0.73	Intermediate Similarity	NPC155332
0.73	Intermediate Similarity	NPC114540
0.73	Intermediate Similarity	NPC238397
0.73	Intermediate Similarity	NPC471363
0.73	Intermediate Similarity	NPC32577
0.7292	Intermediate Similarity	NPC474554
0.7292	Intermediate Similarity	NPC88507
0.7292	Intermediate Similarity	NPC477722
0.7292	Intermediate Similarity	NPC469491
0.7292	Intermediate Similarity	NPC105490
0.7284	Intermediate Similarity	NPC255781
0.7283	Intermediate Similarity	NPC329692
0.7273	Intermediate Similarity	NPC228251
0.7273	Intermediate Similarity	NPC266955
0.7273	Intermediate Similarity	NPC477971
0.7273	Intermediate Similarity	NPC477972
0.7273	Intermediate Similarity	NPC20113
0.7273	Intermediate Similarity	NPC219285
0.7273	Intermediate Similarity	NPC476767
0.7273	Intermediate Similarity	NPC472826
0.7273	Intermediate Similarity	NPC190211
0.7273	Intermediate Similarity	NPC477968
0.7273	Intermediate Similarity	NPC161527
0.7273	Intermediate Similarity	NPC38855
0.7264	Intermediate Similarity	NPC470027
0.7263	Intermediate Similarity	NPC289479
0.7263	Intermediate Similarity	NPC179517
0.7263	Intermediate Similarity	NPC472814
0.7263	Intermediate Similarity	NPC177037
0.7263	Intermediate Similarity	NPC165904
0.7262	Intermediate Similarity	NPC181587
0.7255	Intermediate Similarity	NPC252296
0.7253	Intermediate Similarity	NPC318515
0.7253	Intermediate Similarity	NPC96055
0.7253	Intermediate Similarity	NPC474693
0.725	Intermediate Similarity	NPC226066
0.7238	Intermediate Similarity	NPC470026
0.7234	Intermediate Similarity	NPC309310
0.7234	Intermediate Similarity	NPC5509

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 NPC329630 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	1217
0.2-0.3	4191
0.3-0.4	2624
0.4-0.5	619
0.5-0.6	284
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
0.8046	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7637	Suspended
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4194	Approved
0.7	Intermediate Similarity	NPD4193	Approved
0.7	Intermediate Similarity	NPD4192	Approved
0.7	Intermediate Similarity	NPD4191	Approved
0.6952	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD7638	Approved
0.6778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7503	Approved
0.663	Remote Similarity	NPD7514	Phase 3
0.663	Remote Similarity	NPD7332	Phase 2
0.6629	Remote Similarity	NPD8264	Approved
0.6593	Remote Similarity	NPD7145	Approved
0.6559	Remote Similarity	NPD6902	Approved
0.6552	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD7144	Approved
0.6549	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD7327	Approved
0.6531	Remote Similarity	NPD689	Discontinued
0.6522	Remote Similarity	NPD8033	Approved
0.6505	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7516	Approved
0.6484	Remote Similarity	NPD6925	Approved
0.6484	Remote Similarity	NPD5776	Phase 2
0.6477	Remote Similarity	NPD7151	Approved
0.6477	Remote Similarity	NPD7150	Approved
0.6477	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6437	Remote Similarity	NPD6923	Approved
0.6437	Remote Similarity	NPD6922	Approved
0.6435	Remote Similarity	NPD8377	Approved
0.6435	Remote Similarity	NPD8294	Approved
0.6421	Remote Similarity	NPD6695	Phase 3
0.6379	Remote Similarity	NPD8296	Approved
0.6379	Remote Similarity	NPD8380	Approved
0.6379	Remote Similarity	NPD8335	Approved
0.6379	Remote Similarity	NPD8379	Approved
0.6379	Remote Similarity	NPD8378	Approved
0.6375	Remote Similarity	NPD4219	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6929	Approved
0.6333	Remote Similarity	NPD6924	Approved
0.6333	Remote Similarity	NPD6926	Approved
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD7115	Discovery
0.6304	Remote Similarity	NPD6932	Approved
0.63	Remote Similarity	NPD5785	Approved
0.6277	Remote Similarity	NPD6931	Approved
0.6277	Remote Similarity	NPD6930	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6083	Phase 2
0.6224	Remote Similarity	NPD7521	Approved
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6049	Phase 2
0.6211	Remote Similarity	NPD6898	Phase 1
0.6196	Remote Similarity	NPD6933	Approved
0.6176	Remote Similarity	NPD5779	Approved
0.6176	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD6399	Phase 3
0.6167	Remote Similarity	NPD7507	Approved
0.6162	Remote Similarity	NPD7524	Approved
0.6162	Remote Similarity	NPD7750	Discontinued
0.6154	Remote Similarity	NPD4058	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6132	Remote Similarity	NPD6648	Approved
0.6122	Remote Similarity	NPD1694	Approved
0.6117	Remote Similarity	NPD7748	Approved
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.61	Remote Similarity	NPD6903	Approved
0.61	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6412	Phase 2
0.6087	Remote Similarity	NPD7339	Approved
0.6087	Remote Similarity	NPD6942	Approved
0.6078	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD7515	Phase 2
0.6075	Remote Similarity	NPD5344	Discontinued
0.6064	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4623	Approved
0.6061	Remote Similarity	NPD4519	Discontinued
0.604	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3665	Phase 1
0.602	Remote Similarity	NPD3666	Approved
0.602	Remote Similarity	NPD3133	Approved
0.602	Remote Similarity	NPD4786	Approved
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.5981	Remote Similarity	NPD6404	Discontinued
0.5979	Remote Similarity	NPD3667	Approved
0.5978	Remote Similarity	NPD4687	Approved
0.5978	Remote Similarity	NPD5733	Approved
0.5977	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6882	Approved
0.596	Remote Similarity	NPD1696	Phase 3
0.596	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6893	Approved
0.5943	Remote Similarity	NPD7902	Approved
0.5938	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7509	Discontinued
0.5938	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6079	Approved
0.5922	Remote Similarity	NPD5284	Approved
0.5922	Remote Similarity	NPD7087	Discontinued
0.5922	Remote Similarity	NPD5281	Approved
0.5922	Remote Similarity	NPD5693	Phase 1
0.5918	Remote Similarity	NPD5362	Discontinued
0.5918	Remote Similarity	NPD7154	Phase 3
0.5905	Remote Similarity	NPD5695	Phase 3
0.59	Remote Similarity	NPD5279	Phase 3
0.59	Remote Similarity	NPD3618	Phase 1
0.5893	Remote Similarity	NPD6899	Approved
0.5893	Remote Similarity	NPD6881	Approved
0.5889	Remote Similarity	NPD4137	Phase 3
0.5888	Remote Similarity	NPD5696	Approved
0.5882	Remote Similarity	NPD5328	Approved
0.5882	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5739	Approved
0.5856	Remote Similarity	NPD6402	Approved
0.5856	Remote Similarity	NPD7128	Approved
0.5856	Remote Similarity	NPD6675	Approved
0.5849	Remote Similarity	NPD7839	Suspended
0.5849	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8513	Phase 3
0.5833	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD8516	Approved
0.5833	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD8517	Approved
0.5825	Remote Similarity	NPD5207	Approved
0.5825	Remote Similarity	NPD46	Approved
0.5825	Remote Similarity	NPD7136	Phase 2
0.5825	Remote Similarity	NPD6698	Approved
0.5824	Remote Similarity	NPD4691	Approved
0.5824	Remote Similarity	NPD4747	Approved
0.5806	Remote Similarity	NPD4785	Approved
0.5806	Remote Similarity	NPD4784	Approved
0.5804	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD5363	Approved
0.58	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6883	Approved
0.5789	Remote Similarity	NPD7290	Approved
0.5789	Remote Similarity	NPD7102	Approved
0.5773	Remote Similarity	NPD7525	Registered
0.5773	Remote Similarity	NPD4820	Approved
0.5773	Remote Similarity	NPD4822	Approved
0.5773	Remote Similarity	NPD4821	Approved
0.5773	Remote Similarity	NPD4819	Approved
0.5769	Remote Similarity	NPD6050	Approved
0.5769	Remote Similarity	NPD5694	Approved
0.5761	Remote Similarity	NPD5276	Approved
0.5758	Remote Similarity	NPD5332	Approved
0.5758	Remote Similarity	NPD5331	Approved
0.5758	Remote Similarity	NPD3971	Phase 1
0.5755	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7320	Approved
0.5752	Remote Similarity	NPD6011	Approved
0.5739	Remote Similarity	NPD6847	Approved
0.5739	Remote Similarity	NPD6617	Approved
0.5739	Remote Similarity	NPD6649	Approved
0.5739	Remote Similarity	NPD6869	Approved
0.5739	Remote Similarity	NPD6650	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5729	Remote Similarity	NPD4268	Approved
0.5729	Remote Similarity	NPD4271	Approved
0.5728	Remote Similarity	NPD6673	Approved
0.5728	Remote Similarity	NPD6080	Approved
0.5728	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD4790	Discontinued
0.5714	Remote Similarity	NPD6640	Phase 3
0.5703	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5696	Remote Similarity	NPD4220	Pre-registration
0.569	Remote Similarity	NPD6053	Discontinued
0.569	Remote Similarity	NPD8297	Approved
0.5686	Remote Similarity	NPD3573	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.5673	Remote Similarity	NPD5692	Phase 3
0.5664	Remote Similarity	NPD5701	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