NPASS Compound

Structure

NPC238146 OpenBabel07101718182D 25 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 18 1 0 0 0 0 18 22 1 6 0 0 0 19 21 1 0 0 0 0 19 22 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	390.417
LogP:	4.909
LogD:	3.824
LogS:	-4.144
# Rotatable Bonds:	7
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	4.36
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.43
MDCK Permeability:	2.737316390266642e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	58.0645751953125%
Volume Distribution (VD):	1.155
Pgp-substrate:	31.544404983520508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.592
CYP3A4-inhibitor:	0.392
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	7.55
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.32
Skin Sensitization:	0.409
Carcinogencity:	0.932
Eye Corrosion:	0.515
Eye Irritation:	0.227
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC238146

Natural Product ID:	NPC238146
*Common Name:**	Calcaratarin A
IUPAC Name:	(E)-4-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-2-(2,2-dimethoxyethyl)but-2-enal
Synonyms:
Standard InCHIKey:	KUJKCZZRNAACDH-IEPFJFGQSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-16-8-11-19-21(2,3)12-7-13-22(19,4)18(16)10-9-17(15-23)14-20(24-5)25-6/h9,15,18-20H,1,7-8,10-14H2,2-6H3/b17-9+/t18-,19-,22+/m0/s1
SMILES:	COC(C/C(=CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)/C=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508115
PubChem CID:	10689094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO16667	Curcuma mangga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[16038556]
NPO16667	Curcuma mangga	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	11.5	%	PMID[520957]

☑ 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 NPC238146 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	193
0.1-0.2	1733
0.2-0.3	9509
0.3-0.4	15682
0.4-0.5	8125
0.5-0.6	6359
0.6-0.7	1031
0.7-0.8	54
0.8-0.85	4
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC144947
0.8406	Intermediate Similarity	NPC52449
0.8406	Intermediate Similarity	NPC169275
0.8378	Intermediate Similarity	NPC168975
0.8378	Intermediate Similarity	NPC75485
0.8354	Intermediate Similarity	NPC469
0.8101	Intermediate Similarity	NPC149237
0.7711	Intermediate Similarity	NPC217394
0.7703	Intermediate Similarity	NPC155198
0.7674	Intermediate Similarity	NPC253186
0.7662	Intermediate Similarity	NPC211641
0.7662	Intermediate Similarity	NPC128346
0.7662	Intermediate Similarity	NPC219232
0.7568	Intermediate Similarity	NPC4370
0.7568	Intermediate Similarity	NPC290350
0.75	Intermediate Similarity	NPC59436
0.7432	Intermediate Similarity	NPC185587
0.7407	Intermediate Similarity	NPC283789
0.7349	Intermediate Similarity	NPC142683
0.7297	Intermediate Similarity	NPC268039
0.7294	Intermediate Similarity	NPC2709
0.7284	Intermediate Similarity	NPC115515
0.725	Intermediate Similarity	NPC474463
0.725	Intermediate Similarity	NPC469793
0.725	Intermediate Similarity	NPC4509
0.725	Intermediate Similarity	NPC19907
0.725	Intermediate Similarity	NPC469796
0.7229	Intermediate Similarity	NPC90055
0.7215	Intermediate Similarity	NPC20025
0.7195	Intermediate Similarity	NPC476177
0.7195	Intermediate Similarity	NPC470429
0.7191	Intermediate Similarity	NPC65513
0.7183	Intermediate Similarity	NPC60772
0.7179	Intermediate Similarity	NPC474539
0.7179	Intermediate Similarity	NPC474562
0.7174	Intermediate Similarity	NPC204054
0.7174	Intermediate Similarity	NPC257726
0.716	Intermediate Similarity	NPC470428
0.7143	Intermediate Similarity	NPC470813
0.7111	Intermediate Similarity	NPC474185
0.7108	Intermediate Similarity	NPC474509
0.7097	Intermediate Similarity	NPC473154
0.7093	Intermediate Similarity	NPC300985
0.7079	Intermediate Similarity	NPC159748
0.7079	Intermediate Similarity	NPC101651
0.7073	Intermediate Similarity	NPC476949
0.7067	Intermediate Similarity	NPC107258
0.7059	Intermediate Similarity	NPC472440
0.7059	Intermediate Similarity	NPC307258
0.7	Intermediate Similarity	NPC78527
0.7	Intermediate Similarity	NPC166797
0.6988	Remote Similarity	NPC170793
0.6988	Remote Similarity	NPC90965
0.6966	Remote Similarity	NPC469546
0.6966	Remote Similarity	NPC251528
0.6951	Remote Similarity	NPC219809
0.6951	Remote Similarity	NPC472300
0.6941	Remote Similarity	NPC94200
0.6941	Remote Similarity	NPC200513
0.6933	Remote Similarity	NPC329698
0.6923	Remote Similarity	NPC151722
0.6914	Remote Similarity	NPC65650
0.6905	Remote Similarity	NPC474956
0.6905	Remote Similarity	NPC2482
0.6905	Remote Similarity	NPC473685
0.6897	Remote Similarity	NPC30984
0.6897	Remote Similarity	NPC329630
0.6897	Remote Similarity	NPC472442
0.6889	Remote Similarity	NPC328141
0.6883	Remote Similarity	NPC193770
0.6882	Remote Similarity	NPC319692
0.6882	Remote Similarity	NPC325960
0.6882	Remote Similarity	NPC73858
0.6875	Remote Similarity	NPC476489
0.6875	Remote Similarity	NPC303613
0.6875	Remote Similarity	NPC134077
0.6875	Remote Similarity	NPC12680
0.6875	Remote Similarity	NPC476490
0.6875	Remote Similarity	NPC474228
0.6867	Remote Similarity	NPC228911
0.686	Remote Similarity	NPC22611
0.6854	Remote Similarity	NPC206060
0.6854	Remote Similarity	NPC473229
0.6854	Remote Similarity	NPC474629
0.6854	Remote Similarity	NPC196407
0.6848	Remote Similarity	NPC269729
0.6835	Remote Similarity	NPC251929
0.6835	Remote Similarity	NPC2634
0.6835	Remote Similarity	NPC265782
0.6829	Remote Similarity	NPC26504
0.6824	Remote Similarity	NPC40228
0.6818	Remote Similarity	NPC168248
0.6818	Remote Similarity	NPC118266
0.6813	Remote Similarity	NPC179517
0.6813	Remote Similarity	NPC476187
0.6813	Remote Similarity	NPC165904
0.6813	Remote Similarity	NPC477783
0.6806	Remote Similarity	NPC321568
0.6806	Remote Similarity	NPC208749
0.6806	Remote Similarity	NPC22019
0.6806	Remote Similarity	NPC281986
0.6795	Remote Similarity	NPC260474
0.6795	Remote Similarity	NPC188292
0.679	Remote Similarity	NPC329866
0.679	Remote Similarity	NPC147438
0.679	Remote Similarity	NPC474796
0.679	Remote Similarity	NPC474797
0.679	Remote Similarity	NPC309852
0.6786	Remote Similarity	NPC190211
0.6782	Remote Similarity	NPC472265
0.6778	Remote Similarity	NPC474396
0.6778	Remote Similarity	NPC50070
0.6778	Remote Similarity	NPC50488
0.6778	Remote Similarity	NPC79027
0.6778	Remote Similarity	NPC471654
0.6778	Remote Similarity	NPC477973
0.6774	Remote Similarity	NPC274417
0.6771	Remote Similarity	NPC63249
0.6757	Remote Similarity	NPC127582
0.6753	Remote Similarity	NPC259156
0.6753	Remote Similarity	NPC242945
0.675	Remote Similarity	NPC304983
0.675	Remote Similarity	NPC72343
0.675	Remote Similarity	NPC257618
0.675	Remote Similarity	NPC190035
0.675	Remote Similarity	NPC21944
0.675	Remote Similarity	NPC54123
0.675	Remote Similarity	NPC133253
0.6742	Remote Similarity	NPC288952
0.6739	Remote Similarity	NPC166346
0.6739	Remote Similarity	NPC267266
0.6739	Remote Similarity	NPC277721
0.6709	Remote Similarity	NPC256846
0.6709	Remote Similarity	NPC139397
0.6705	Remote Similarity	NPC86316
0.6705	Remote Similarity	NPC329738
0.6705	Remote Similarity	NPC106416
0.6705	Remote Similarity	NPC65661
0.6705	Remote Similarity	NPC33881
0.6705	Remote Similarity	NPC133652
0.6703	Remote Similarity	NPC477782
0.6702	Remote Similarity	NPC112654
0.6667	Remote Similarity	NPC470906
0.6667	Remote Similarity	NPC60565
0.6667	Remote Similarity	NPC4827
0.6667	Remote Similarity	NPC118423
0.6667	Remote Similarity	NPC304968
0.6667	Remote Similarity	NPC470165
0.6667	Remote Similarity	NPC198240
0.6667	Remote Similarity	NPC474976
0.6667	Remote Similarity	NPC251705
0.6667	Remote Similarity	NPC42476
0.6667	Remote Similarity	NPC128488
0.6667	Remote Similarity	NPC239098
0.6667	Remote Similarity	NPC176107
0.6667	Remote Similarity	NPC105197
0.6667	Remote Similarity	NPC35574
0.6667	Remote Similarity	NPC474790
0.6667	Remote Similarity	NPC291665
0.6632	Remote Similarity	NPC476768
0.663	Remote Similarity	NPC230064
0.663	Remote Similarity	NPC72845
0.6629	Remote Similarity	NPC195640
0.6629	Remote Similarity	NPC211892
0.6629	Remote Similarity	NPC220478
0.6628	Remote Similarity	NPC170303
0.6628	Remote Similarity	NPC229584
0.6628	Remote Similarity	NPC278459
0.6628	Remote Similarity	NPC474955
0.6628	Remote Similarity	NPC121984
0.6628	Remote Similarity	NPC475665
0.6628	Remote Similarity	NPC159148
0.6628	Remote Similarity	NPC474085
0.6628	Remote Similarity	NPC14203
0.6627	Remote Similarity	NPC41017
0.6627	Remote Similarity	NPC899
0.6627	Remote Similarity	NPC470525
0.6627	Remote Similarity	NPC69408
0.6625	Remote Similarity	NPC260040
0.6625	Remote Similarity	NPC159577
0.6625	Remote Similarity	NPC307176
0.6625	Remote Similarity	NPC282593
0.6625	Remote Similarity	NPC35734
0.6623	Remote Similarity	NPC251118
0.6623	Remote Similarity	NPC183422
0.6596	Remote Similarity	NPC476519
0.6593	Remote Similarity	NPC293044
0.6593	Remote Similarity	NPC474844
0.6593	Remote Similarity	NPC174342
0.6593	Remote Similarity	NPC184663
0.6593	Remote Similarity	NPC177141
0.6591	Remote Similarity	NPC33913
0.6591	Remote Similarity	NPC71626
0.6591	Remote Similarity	NPC470812
0.6591	Remote Similarity	NPC312660
0.6591	Remote Similarity	NPC470800
0.6591	Remote Similarity	NPC476412
0.6591	Remote Similarity	NPC96055
0.6591	Remote Similarity	NPC139566
0.6588	Remote Similarity	NPC327674

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 NPC238146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1961
0.2-0.3	4703
0.3-0.4	1702
0.4-0.5	333
0.5-0.6	241
0.6-0.7	32
0.7-0.8	1
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
0.6941	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4691	Approved
0.6709	Remote Similarity	NPD4137	Phase 3
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6625	Remote Similarity	NPD4747	Approved
0.6585	Remote Similarity	NPD4058	Approved
0.6512	Remote Similarity	NPD4695	Discontinued
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6386	Remote Similarity	NPD5733	Approved
0.6341	Remote Similarity	NPD5276	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6264	Remote Similarity	NPD3618	Phase 1
0.6224	Remote Similarity	NPD4225	Approved
0.6222	Remote Similarity	NPD3666	Approved
0.6222	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3665	Phase 1
0.6222	Remote Similarity	NPD4786	Approved
0.6222	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD6686	Approved
0.6211	Remote Similarity	NPD6399	Phase 3
0.6196	Remote Similarity	NPD3573	Approved
0.619	Remote Similarity	NPD4687	Approved
0.618	Remote Similarity	NPD3667	Approved
0.6173	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7748	Approved
0.6122	Remote Similarity	NPD7902	Approved
0.6117	Remote Similarity	NPD6412	Phase 2
0.6105	Remote Similarity	NPD6079	Approved
0.6105	Remote Similarity	NPD7515	Phase 2
0.6098	Remote Similarity	NPD6923	Approved
0.6098	Remote Similarity	NPD6922	Approved
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD8028	Phase 2
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD5328	Approved
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6053	Remote Similarity	NPD287	Approved
0.6044	Remote Similarity	NPD3668	Phase 3
0.6024	Remote Similarity	NPD7143	Approved
0.6024	Remote Similarity	NPD7144	Approved
0.6023	Remote Similarity	NPD4195	Approved
0.602	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5978	Remote Similarity	NPD5329	Approved
0.596	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD6084	Phase 2
0.5957	Remote Similarity	NPD5208	Approved
0.5955	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7150	Approved
0.5952	Remote Similarity	NPD7151	Approved
0.5952	Remote Similarity	NPD7152	Approved
0.5938	Remote Similarity	NPD7637	Suspended
0.593	Remote Similarity	NPD8039	Approved
0.593	Remote Similarity	NPD6942	Approved
0.593	Remote Similarity	NPD7339	Approved
0.5918	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD4629	Approved
0.5914	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5279	Phase 3
0.5914	Remote Similarity	NPD6098	Approved
0.59	Remote Similarity	NPD5696	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5895	Remote Similarity	NPD4753	Phase 2
0.5895	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4197	Approved
0.5862	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6933	Approved
0.5859	Remote Similarity	NPD7732	Phase 3
0.5843	Remote Similarity	NPD7645	Phase 2
0.5842	Remote Similarity	NPD7639	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.5823	Remote Similarity	NPD4193	Approved
0.5823	Remote Similarity	NPD4191	Approved
0.5823	Remote Similarity	NPD4192	Approved
0.5823	Remote Similarity	NPD4194	Approved
0.5816	Remote Similarity	NPD6001	Approved
0.5795	Remote Similarity	NPD6932	Approved
0.5795	Remote Similarity	NPD5776	Phase 2
0.5795	Remote Similarity	NPD6925	Approved
0.5773	Remote Similarity	NPD5693	Phase 1
0.5773	Remote Similarity	NPD6050	Approved
0.5761	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4788	Approved
0.5758	Remote Similarity	NPD5695	Phase 3
0.5747	Remote Similarity	NPD8264	Approved
0.5745	Remote Similarity	NPD4693	Phase 3
0.5745	Remote Similarity	NPD4519	Discontinued
0.5745	Remote Similarity	NPD4623	Approved
0.5745	Remote Similarity	NPD4138	Approved
0.5745	Remote Similarity	NPD4690	Approved
0.5745	Remote Similarity	NPD4689	Approved
0.5745	Remote Similarity	NPD5690	Phase 2
0.5745	Remote Similarity	NPD5205	Approved
0.5745	Remote Similarity	NPD4688	Approved
0.573	Remote Similarity	NPD7145	Approved
0.573	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.573	Remote Similarity	NPD3617	Approved
0.5729	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD4202	Approved
0.57	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5221	Approved
0.57	Remote Similarity	NPD5222	Approved
0.5688	Remote Similarity	NPD6882	Approved
0.567	Remote Similarity	NPD5785	Approved
0.567	Remote Similarity	NPD5692	Phase 3
0.5667	Remote Similarity	NPD6929	Approved
0.5667	Remote Similarity	NPD6683	Phase 2
0.5652	Remote Similarity	NPD5209	Approved
0.5644	Remote Similarity	NPD5173	Approved
0.5632	Remote Similarity	NPD4784	Approved
0.5632	Remote Similarity	NPD4785	Approved
0.5612	Remote Similarity	NPD5284	Approved
0.5612	Remote Similarity	NPD5281	Approved
0.5612	Remote Similarity	NPD5694	Approved
0.5612	Remote Similarity	NPD6411	Approved
0.561	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6881	Approved
0.5607	Remote Similarity	NPD6899	Approved
0.5604	Remote Similarity	NPD7525	Registered
0.5604	Remote Similarity	NPD7509	Discontinued
0.5604	Remote Similarity	NPD6931	Approved
0.5604	Remote Similarity	NPD6930	Phase 2
0.5604	Remote Similarity	NPD7514	Phase 3
0.5604	Remote Similarity	NPD7332	Phase 2

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