NPASS Compound

Structure

NPC471159 OpenBabel07101718242D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0981 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 1.6340 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 6 2 0 0 0 0 2 13 2 0 0 0 0 6 20 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 20 1 1 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	3.692
LogD:	3.441
LogS:	-4.248
# Rotatable Bonds:	4
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	4.8
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.178
MDCK Permeability:	2.542408401495777e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.297
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.478
Plasma Protein Binding (PPB):	76.10282897949219%
Volume Distribution (VD):	0.393
Pgp-substrate:	21.882431030273438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.171
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.544
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	1.662
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.722
Carcinogencity:	0.459
Eye Corrosion:	0.89
Eye Irritation:	0.925
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC471159

Natural Product ID:	NPC471159
*Common Name:**	(12S,13R)-12,13-Epoxylabda-8(17),14-Dien-19-Oic Acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[[(2S,3R)-3-ethenyl-3-methyloxiran-2-yl]methyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	WGURGXZGVSMKKG-YDMLNEHTSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-6-20(5)16(23-20)12-14-13(2)8-9-15-18(14,3)10-7-11-19(15,4)17(21)22/h6,14-16H,1-2,7-12H2,3-5H3,(H,21,22)/t14-,15+,16-,18+,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)O[C@H]1C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385632
PubChem CID:	71725777
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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[465911]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[465911]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[465911]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[465911]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[465911]

☑ 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 NPC471159 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	182
0.1-0.2	1234
0.2-0.3	4975
0.3-0.4	14429
0.4-0.5	8681
0.5-0.6	7298
0.6-0.7	5116
0.7-0.8	762
0.8-0.85	16
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123880
0.8734	High Similarity	NPC247783
0.8734	High Similarity	NPC269543
0.8462	Intermediate Similarity	NPC18819
0.8462	Intermediate Similarity	NPC46610
0.8415	Intermediate Similarity	NPC229584
0.8415	Intermediate Similarity	NPC14203
0.8395	Intermediate Similarity	NPC263951
0.8353	Intermediate Similarity	NPC9231
0.8353	Intermediate Similarity	NPC185638
0.8295	Intermediate Similarity	NPC303697
0.8193	Intermediate Similarity	NPC48673
0.8193	Intermediate Similarity	NPC20096
0.8171	Intermediate Similarity	NPC476438
0.8171	Intermediate Similarity	NPC192999
0.814	Intermediate Similarity	NPC472505
0.814	Intermediate Similarity	NPC85698
0.809	Intermediate Similarity	NPC49420
0.8077	Intermediate Similarity	NPC91369
0.8046	Intermediate Similarity	NPC181103
0.8046	Intermediate Similarity	NPC470012
0.8046	Intermediate Similarity	NPC305029
0.8025	Intermediate Similarity	NPC476601
0.8023	Intermediate Similarity	NPC106416
0.8023	Intermediate Similarity	NPC86316
0.8023	Intermediate Similarity	NPC65661
0.7976	Intermediate Similarity	NPC327002
0.7976	Intermediate Similarity	NPC209318
0.7976	Intermediate Similarity	NPC40228
0.7976	Intermediate Similarity	NPC223330
0.7976	Intermediate Similarity	NPC38642
0.7975	Intermediate Similarity	NPC72343
0.7957	Intermediate Similarity	NPC98868
0.7957	Intermediate Similarity	NPC316598
0.7955	Intermediate Similarity	NPC24816
0.7931	Intermediate Similarity	NPC82979
0.7931	Intermediate Similarity	NPC329692
0.7931	Intermediate Similarity	NPC477920
0.7927	Intermediate Similarity	NPC474433
0.7912	Intermediate Similarity	NPC38830
0.7889	Intermediate Similarity	NPC177037
0.7889	Intermediate Similarity	NPC472814
0.7882	Intermediate Similarity	NPC226988
0.7865	Intermediate Similarity	NPC471342
0.7865	Intermediate Similarity	NPC469866
0.7865	Intermediate Similarity	NPC116620
0.7849	Intermediate Similarity	NPC136781
0.7841	Intermediate Similarity	NPC128644
0.7841	Intermediate Similarity	NPC312561
0.7831	Intermediate Similarity	NPC239098
0.7831	Intermediate Similarity	NPC321514
0.7831	Intermediate Similarity	NPC179028
0.7826	Intermediate Similarity	NPC209355
0.7821	Intermediate Similarity	NPC36616
0.7821	Intermediate Similarity	NPC290445
0.7805	Intermediate Similarity	NPC69143
0.7802	Intermediate Similarity	NPC169343
0.7802	Intermediate Similarity	NPC139692
0.7791	Intermediate Similarity	NPC470948
0.7791	Intermediate Similarity	NPC23748
0.7791	Intermediate Similarity	NPC49208
0.7791	Intermediate Similarity	NPC312480
0.7791	Intermediate Similarity	NPC170862
0.7791	Intermediate Similarity	NPC471037
0.7778	Intermediate Similarity	NPC103958
0.7778	Intermediate Similarity	NPC71152
0.7778	Intermediate Similarity	NPC283908
0.7778	Intermediate Similarity	NPC183503
0.7778	Intermediate Similarity	NPC198818
0.7778	Intermediate Similarity	NPC237591
0.7778	Intermediate Similarity	NPC3753
0.7778	Intermediate Similarity	NPC161923
0.7778	Intermediate Similarity	NPC51486
0.7765	Intermediate Similarity	NPC473420
0.7753	Intermediate Similarity	NPC477128
0.7742	Intermediate Similarity	NPC473964
0.7738	Intermediate Similarity	NPC327674
0.7738	Intermediate Similarity	NPC100906
0.7727	Intermediate Similarity	NPC475007
0.7727	Intermediate Similarity	NPC325594
0.7727	Intermediate Similarity	NPC73038
0.7717	Intermediate Similarity	NPC476415
0.7711	Intermediate Similarity	NPC283619
0.7711	Intermediate Similarity	NPC469867
0.7701	Intermediate Similarity	NPC139566
0.7701	Intermediate Similarity	NPC263974
0.7701	Intermediate Similarity	NPC219011
0.7701	Intermediate Similarity	NPC470011
0.7701	Intermediate Similarity	NPC97505
0.7692	Intermediate Similarity	NPC233345
0.7692	Intermediate Similarity	NPC186363
0.7684	Intermediate Similarity	NPC476303
0.7683	Intermediate Similarity	NPC476844
0.7683	Intermediate Similarity	NPC192540
0.7683	Intermediate Similarity	NPC39362
0.7683	Intermediate Similarity	NPC279666
0.7674	Intermediate Similarity	NPC476984
0.7674	Intermediate Similarity	NPC200513
0.7674	Intermediate Similarity	NPC178676
0.7674	Intermediate Similarity	NPC474605
0.7674	Intermediate Similarity	NPC476292
0.7674	Intermediate Similarity	NPC73882
0.7674	Intermediate Similarity	NPC475395
0.7674	Intermediate Similarity	NPC170985
0.7667	Intermediate Similarity	NPC474396
0.7667	Intermediate Similarity	NPC174342
0.7667	Intermediate Similarity	NPC128496
0.7667	Intermediate Similarity	NPC50488
0.7667	Intermediate Similarity	NPC5509
0.766	Intermediate Similarity	NPC285513
0.766	Intermediate Similarity	NPC473963
0.766	Intermediate Similarity	NPC474343
0.766	Intermediate Similarity	NPC254496
0.7654	Intermediate Similarity	NPC472813
0.7654	Intermediate Similarity	NPC177826
0.7647	Intermediate Similarity	NPC233332
0.7647	Intermediate Similarity	NPC195424
0.764	Intermediate Similarity	NPC476932
0.764	Intermediate Similarity	NPC231599
0.764	Intermediate Similarity	NPC171722
0.764	Intermediate Similarity	NPC175293
0.7634	Intermediate Similarity	NPC293052
0.7634	Intermediate Similarity	NPC157686
0.7634	Intermediate Similarity	NPC90014
0.7634	Intermediate Similarity	NPC295347
0.7634	Intermediate Similarity	NPC33473
0.7634	Intermediate Similarity	NPC259042
0.7625	Intermediate Similarity	NPC235586
0.7619	Intermediate Similarity	NPC474341
0.7619	Intermediate Similarity	NPC35574
0.7619	Intermediate Similarity	NPC321690
0.7619	Intermediate Similarity	NPC59436
0.7619	Intermediate Similarity	NPC470905
0.7619	Intermediate Similarity	NPC476986
0.7614	Intermediate Similarity	NPC329738
0.7614	Intermediate Similarity	NPC269638
0.7614	Intermediate Similarity	NPC476602
0.7614	Intermediate Similarity	NPC52628
0.7614	Intermediate Similarity	NPC283733
0.7609	Intermediate Similarity	NPC115021
0.7609	Intermediate Similarity	NPC199543
0.7604	Intermediate Similarity	NPC475958
0.759	Intermediate Similarity	NPC92489
0.759	Intermediate Similarity	NPC271070
0.759	Intermediate Similarity	NPC104806
0.759	Intermediate Similarity	NPC20466
0.7586	Intermediate Similarity	NPC311070
0.7586	Intermediate Similarity	NPC245866
0.7586	Intermediate Similarity	NPC193198
0.7586	Intermediate Similarity	NPC222358
0.7586	Intermediate Similarity	NPC243347
0.7586	Intermediate Similarity	NPC194637
0.7582	Intermediate Similarity	NPC477782
0.7582	Intermediate Similarity	NPC310479
0.7582	Intermediate Similarity	NPC281942
0.7582	Intermediate Similarity	NPC232426
0.7582	Intermediate Similarity	NPC182136
0.7582	Intermediate Similarity	NPC214844
0.7582	Intermediate Similarity	NPC232202
0.7582	Intermediate Similarity	NPC158488
0.7582	Intermediate Similarity	NPC476369
0.7582	Intermediate Similarity	NPC474728
0.7582	Intermediate Similarity	NPC476437
0.7579	Intermediate Similarity	NPC124703
0.7579	Intermediate Similarity	NPC473155
0.7579	Intermediate Similarity	NPC234617
0.7564	Intermediate Similarity	NPC103734
0.7561	Intermediate Similarity	NPC255168
0.7561	Intermediate Similarity	NPC476046
0.7561	Intermediate Similarity	NPC166797
0.7561	Intermediate Similarity	NPC241854
0.7561	Intermediate Similarity	NPC251970
0.7558	Intermediate Similarity	NPC90055
0.7558	Intermediate Similarity	NPC475951
0.7558	Intermediate Similarity	NPC14151
0.7558	Intermediate Similarity	NPC325031
0.7558	Intermediate Similarity	NPC142163
0.7558	Intermediate Similarity	NPC232625
0.7556	Intermediate Similarity	NPC50847
0.7556	Intermediate Similarity	NPC250687
0.7556	Intermediate Similarity	NPC215831
0.7556	Intermediate Similarity	NPC255176
0.7556	Intermediate Similarity	NPC229407
0.7556	Intermediate Similarity	NPC254572
0.7556	Intermediate Similarity	NPC48824
0.7553	Intermediate Similarity	NPC93245
0.7553	Intermediate Similarity	NPC29952
0.7553	Intermediate Similarity	NPC242848
0.7553	Intermediate Similarity	NPC234993
0.7553	Intermediate Similarity	NPC134072
0.7553	Intermediate Similarity	NPC284518
0.7529	Intermediate Similarity	NPC242767
0.7529	Intermediate Similarity	NPC476177
0.7529	Intermediate Similarity	NPC231431
0.7528	Intermediate Similarity	NPC6979
0.7528	Intermediate Similarity	NPC473226
0.7528	Intermediate Similarity	NPC155011
0.7528	Intermediate Similarity	NPC476104
0.7528	Intermediate Similarity	NPC202394
0.7528	Intermediate Similarity	NPC324063

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 NPC471159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1604
0.2-0.3	3847
0.3-0.4	2350
0.4-0.5	706
0.5-0.6	288
0.6-0.7	179
0.7-0.8	4
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
0.7674	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7128	Intermediate Similarity	NPD6411	Approved
0.7111	Intermediate Similarity	NPD4786	Approved
0.7103	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD8039	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD1694	Approved
0.6989	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6903	Approved
0.697	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD5693	Phase 1
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD6084	Phase 2
0.6939	Remote Similarity	NPD6083	Phase 2
0.6939	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD3133	Approved
0.6915	Remote Similarity	NPD6101	Approved
0.6915	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5695	Phase 3
0.6882	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.6875	Remote Similarity	NPD5779	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.686	Remote Similarity	NPD3702	Approved
0.6854	Remote Similarity	NPD4695	Discontinued
0.6842	Remote Similarity	NPD46	Approved
0.6842	Remote Similarity	NPD6698	Approved
0.6827	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6686	Approved
0.6813	Remote Similarity	NPD4788	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6774	Remote Similarity	NPD3618	Phase 1
0.6774	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD4519	Discontinued
0.6771	Remote Similarity	NPD7637	Suspended
0.6762	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3668	Phase 3
0.6737	Remote Similarity	NPD6051	Approved
0.6735	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5697	Approved
0.6703	Remote Similarity	NPD4221	Approved
0.6703	Remote Similarity	NPD4223	Phase 3
0.6698	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD6008	Approved
0.6635	Remote Similarity	NPD6675	Approved
0.6635	Remote Similarity	NPD6402	Approved
0.6635	Remote Similarity	NPD7128	Approved
0.6635	Remote Similarity	NPD5739	Approved
0.6633	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5208	Approved
0.663	Remote Similarity	NPD7154	Phase 3
0.663	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD6014	Approved
0.6604	Remote Similarity	NPD6013	Approved
0.6598	Remote Similarity	NPD6079	Approved
0.6598	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5279	Phase 3
0.6593	Remote Similarity	NPD5369	Approved
0.6585	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5701	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5328	Approved
0.6562	Remote Similarity	NPD4753	Phase 2
0.6562	Remote Similarity	NPD6080	Approved
0.6562	Remote Similarity	NPD6904	Approved
0.6562	Remote Similarity	NPD1695	Approved
0.6562	Remote Similarity	NPD6673	Approved
0.6559	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6926	Approved
0.6552	Remote Similarity	NPD6924	Approved
0.6542	Remote Similarity	NPD7102	Approved
0.6542	Remote Similarity	NPD7290	Approved
0.6542	Remote Similarity	NPD6883	Approved
0.6531	Remote Similarity	NPD4202	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6512	Remote Similarity	NPD5777	Approved
0.6509	Remote Similarity	NPD7320	Approved
0.6506	Remote Similarity	NPD4224	Phase 2
0.6495	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5329	Approved
0.6481	Remote Similarity	NPD6869	Approved
0.6481	Remote Similarity	NPD6649	Approved
0.6481	Remote Similarity	NPD6617	Approved
0.6481	Remote Similarity	NPD8130	Phase 1
0.6481	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD6650	Approved
0.6465	Remote Similarity	NPD6001	Approved
0.6452	Remote Similarity	NPD6695	Phase 3
0.6449	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD5694	Approved
0.6422	Remote Similarity	NPD6882	Approved
0.6422	Remote Similarity	NPD8297	Approved
0.6421	Remote Similarity	NPD4693	Phase 3
0.6421	Remote Similarity	NPD4688	Approved
0.6421	Remote Similarity	NPD5690	Phase 2
0.6421	Remote Similarity	NPD5205	Approved
0.6421	Remote Similarity	NPD4689	Approved
0.6421	Remote Similarity	NPD4690	Approved
0.6421	Remote Similarity	NPD4138	Approved
0.6415	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5344	Discontinued
0.6404	Remote Similarity	NPD6117	Approved
0.6404	Remote Similarity	NPD6933	Approved
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5210	Approved
0.64	Remote Similarity	NPD4629	Approved
0.6386	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7632	Discontinued
0.6346	Remote Similarity	NPD5211	Phase 2
0.6344	Remote Similarity	NPD6435	Approved
0.6344	Remote Similarity	NPD4270	Approved
0.6344	Remote Similarity	NPD4269	Approved
0.6344	Remote Similarity	NPD5209	Approved
0.6337	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5222	Approved
0.6337	Remote Similarity	NPD5221	Approved
0.6333	Remote Similarity	NPD6116	Phase 1
0.633	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7838	Discovery
0.6327	Remote Similarity	NPD5692	Phase 3
0.6311	Remote Similarity	NPD5285	Approved
0.6311	Remote Similarity	NPD4696	Approved
0.6311	Remote Similarity	NPD5286	Approved
0.6311	Remote Similarity	NPD6648	Approved
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD6930	Phase 2
0.6304	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD6931	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD5282	Discontinued
0.6292	Remote Similarity	NPD7339	Approved
0.6292	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3698	Phase 2
0.6275	Remote Similarity	NPD5173	Approved
0.6275	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD6053	Discontinued
0.6264	Remote Similarity	NPD6115	Approved
0.6264	Remote Similarity	NPD6697	Approved
0.6264	Remote Similarity	NPD3617	Approved
0.6264	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6118	Approved
0.6264	Remote Similarity	NPD6114	Approved
0.6263	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD4694	Approved
0.625	Remote Similarity	NPD5786	Approved
0.6239	Remote Similarity	NPD6371	Approved
0.6226	Remote Similarity	NPD5141	Approved
0.6216	Remote Similarity	NPD4632	Approved
0.6211	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7143	Approved
0.6207	Remote Similarity	NPD7144	Approved
0.6207	Remote Similarity	NPD4244	Approved
0.6207	Remote Similarity	NPD4245	Approved
0.6196	Remote Similarity	NPD4195	Approved
0.6196	Remote Similarity	NPD6929	Approved
0.6196	Remote Similarity	NPD7645	Phase 2
0.6195	Remote Similarity	NPD6317	Approved
0.619	Remote Similarity	NPD5224	Approved
0.619	Remote Similarity	NPD5225	Approved
0.619	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD5226	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