NPASS Compound

Structure

NPC53555 OpenBabel07101718242D 30 32 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3176 -2.3849 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 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 3.4641 -1.0000 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 6.7788 -0.6636 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 2.5981 -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 6.1097 -1.4067 0.0000 C 0 0 0 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 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 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 -0.8660 1.5000 0.0000 C 0 0 2 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 -2.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6856 1.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 2 0 0 0 0 3 17 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 14 26 1 0 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 18 25 1 1 0 0 0 19 27 1 1 0 0 0 20 23 1 0 0 0 0 20 28 1 6 0 0 0 21 29 2 0 0 0 0 21 30 1 0 0 0 0 22 19 1 1 0 0 0 22 30 1 0 0 0 0 23 24 1 1 0 0 0 23 25 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:	418.27
Volume:	448.692
LogP:	3.6
LogD:	3.788
LogS:	-4.085
# Rotatable Bonds:	6
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	5.174
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.135
MDCK Permeability:	1.693951344350353e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.164
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.13

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.575
Plasma Protein Binding (PPB):	88.53804779052734%
Volume Distribution (VD):	1.314
Pgp-substrate:	10.381288528442383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	8.517
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.19
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.6
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.098
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.015
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: NPC53555

Natural Product ID:	NPC53555
*Common Name:**	6Alpha,15(S),23-Trihydroxy-Labd-8(22),13(14),17-Trien-16(S),19-Olide
IUPAC Name:	(2S)-2-[(E,1S)-5-[(1S,4S,4aR,5R,8aR)-4-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxy-3-methylpent-2-enyl]-3-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	TWNFADMNOYVISL-MONHHEJASA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-15(11-19(27)22-17(3)13-21(29)30-22)7-8-18-16(2)12-20(28)23-24(4,14-26)9-6-10-25(18,23)5/h11,13,18-20,22-23,26-28H,2,6-10,12,14H2,1,3-5H3/b15-11+/t18-,19-,20-,22-,23-,24-,25+/m0/s1
SMILES:	OC[C@]1(C)CCC[C@]2([C@H]1[C@@H](O)CC(=C)[C@@H]2CC/C(=C/[C@@H]([C@H]1OC(=O)C=C1C)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523078
PubChem CID:	44157610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]

☑ 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
Kd	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	2000.0	nM	PMID[525054]

☑ 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 NPC53555 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	184
0.1-0.2	1164
0.2-0.3	3808
0.3-0.4	8077
0.4-0.5	13783
0.5-0.6	7048
0.6-0.7	6376
0.7-0.8	2015
0.8-0.85	168
0.85-0.9	60
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC38855
0.9318	High Similarity	NPC78973
0.908	High Similarity	NPC131813
0.9043	High Similarity	NPC303559
0.9022	High Similarity	NPC473153
0.9	High Similarity	NPC472811
0.8977	High Similarity	NPC473891
0.8913	High Similarity	NPC276110
0.8901	High Similarity	NPC472812
0.883	High Similarity	NPC159763
0.883	High Similarity	NPC278386
0.883	High Similarity	NPC124512
0.8804	High Similarity	NPC105490
0.8791	High Similarity	NPC329842
0.8776	High Similarity	NPC67321
0.8776	High Similarity	NPC187435
0.875	High Similarity	NPC35933
0.8736	High Similarity	NPC311070
0.8723	High Similarity	NPC73911
0.8721	High Similarity	NPC170303
0.8721	High Similarity	NPC159148
0.8696	High Similarity	NPC205034
0.8696	High Similarity	NPC152778
0.8696	High Similarity	NPC162615
0.8696	High Similarity	NPC7349
0.8687	High Similarity	NPC38948
0.8681	High Similarity	NPC182136
0.8681	High Similarity	NPC310479
0.8681	High Similarity	NPC280149
0.8681	High Similarity	NPC221111
0.866	High Similarity	NPC281378
0.8652	High Similarity	NPC475069
0.8652	High Similarity	NPC175145
0.8646	High Similarity	NPC11974
0.8646	High Similarity	NPC472554
0.8636	High Similarity	NPC96055
0.8617	High Similarity	NPC16967
0.8617	High Similarity	NPC88009
0.8605	High Similarity	NPC281880
0.8602	High Similarity	NPC57117
0.8602	High Similarity	NPC470255
0.86	High Similarity	NPC206618
0.8587	High Similarity	NPC72845
0.8571	High Similarity	NPC20946
0.8571	High Similarity	NPC50488
0.8571	High Similarity	NPC474396
0.8571	High Similarity	NPC246028
0.8571	High Similarity	NPC82876
0.8557	High Similarity	NPC472815
0.8557	High Similarity	NPC472552
0.8556	High Similarity	NPC166857
0.8542	High Similarity	NPC474190
0.8542	High Similarity	NPC473510
0.8542	High Similarity	NPC324841
0.8539	High Similarity	NPC474013
0.8526	High Similarity	NPC210337
0.8523	High Similarity	NPC42476
0.8523	High Similarity	NPC476927
0.8511	High Similarity	NPC472441
0.85	High Similarity	NPC306265
0.8495	Intermediate Similarity	NPC139692
0.8462	Intermediate Similarity	NPC472810
0.8462	Intermediate Similarity	NPC93411
0.8462	Intermediate Similarity	NPC472809
0.8454	Intermediate Similarity	NPC475617
0.8444	Intermediate Similarity	NPC329692
0.8438	Intermediate Similarity	NPC278673
0.8438	Intermediate Similarity	NPC473154
0.8438	Intermediate Similarity	NPC275086
0.8438	Intermediate Similarity	NPC325229
0.8427	Intermediate Similarity	NPC102048
0.8421	Intermediate Similarity	NPC134072
0.8421	Intermediate Similarity	NPC242848
0.8421	Intermediate Similarity	NPC234993
0.8421	Intermediate Similarity	NPC165632
0.8409	Intermediate Similarity	NPC471218
0.8409	Intermediate Similarity	NPC256112
0.8409	Intermediate Similarity	NPC2524
0.8404	Intermediate Similarity	NPC472416
0.8404	Intermediate Similarity	NPC191521
0.8404	Intermediate Similarity	NPC469697
0.8404	Intermediate Similarity	NPC472360
0.84	Intermediate Similarity	NPC471205
0.8367	Intermediate Similarity	NPC109195
0.8367	Intermediate Similarity	NPC273668
0.8367	Intermediate Similarity	NPC476081
0.8367	Intermediate Similarity	NPC11956
0.8367	Intermediate Similarity	NPC475038
0.8367	Intermediate Similarity	NPC258547
0.8367	Intermediate Similarity	NPC283343
0.8352	Intermediate Similarity	NPC131329
0.8352	Intermediate Similarity	NPC245004
0.8351	Intermediate Similarity	NPC230546
0.8333	Intermediate Similarity	NPC231751
0.8333	Intermediate Similarity	NPC471795
0.8333	Intermediate Similarity	NPC51499
0.8333	Intermediate Similarity	NPC30984
0.8333	Intermediate Similarity	NPC177047
0.8333	Intermediate Similarity	NPC205143
0.8317	Intermediate Similarity	NPC181994
0.8317	Intermediate Similarity	NPC50124
0.8317	Intermediate Similarity	NPC88701
0.8315	Intermediate Similarity	NPC79945
0.8315	Intermediate Similarity	NPC23748
0.8315	Intermediate Similarity	NPC49208
0.83	Intermediate Similarity	NPC88349
0.8298	Intermediate Similarity	NPC110022
0.8298	Intermediate Similarity	NPC472641
0.8298	Intermediate Similarity	NPC472640
0.8295	Intermediate Similarity	NPC25554
0.8295	Intermediate Similarity	NPC475944
0.8283	Intermediate Similarity	NPC474124
0.8283	Intermediate Similarity	NPC23584
0.8283	Intermediate Similarity	NPC472821
0.828	Intermediate Similarity	NPC472642
0.8265	Intermediate Similarity	NPC473160
0.8261	Intermediate Similarity	NPC474629
0.8261	Intermediate Similarity	NPC291665
0.8247	Intermediate Similarity	NPC218107
0.8247	Intermediate Similarity	NPC474440
0.8229	Intermediate Similarity	NPC211810
0.8229	Intermediate Similarity	NPC162346
0.8229	Intermediate Similarity	NPC284194
0.8229	Intermediate Similarity	NPC471765
0.8229	Intermediate Similarity	NPC221801
0.8222	Intermediate Similarity	NPC306951
0.8218	Intermediate Similarity	NPC122816
0.8218	Intermediate Similarity	NPC475176
0.8218	Intermediate Similarity	NPC473586
0.8211	Intermediate Similarity	NPC469491
0.8211	Intermediate Similarity	NPC104925
0.8211	Intermediate Similarity	NPC298973
0.82	Intermediate Similarity	NPC473543
0.8191	Intermediate Similarity	NPC78594
0.8182	Intermediate Similarity	NPC295791
0.8182	Intermediate Similarity	NPC121423
0.8182	Intermediate Similarity	NPC475344
0.8182	Intermediate Similarity	NPC476471
0.8172	Intermediate Similarity	NPC470734
0.8172	Intermediate Similarity	NPC473647
0.8163	Intermediate Similarity	NPC251680
0.8163	Intermediate Similarity	NPC472826
0.8163	Intermediate Similarity	NPC16601
0.8152	Intermediate Similarity	NPC476948
0.8152	Intermediate Similarity	NPC476600
0.8144	Intermediate Similarity	NPC224356
0.8144	Intermediate Similarity	NPC132753
0.8144	Intermediate Similarity	NPC474343
0.8144	Intermediate Similarity	NPC473244
0.8144	Intermediate Similarity	NPC253826
0.8144	Intermediate Similarity	NPC151681
0.8144	Intermediate Similarity	NPC121402
0.8144	Intermediate Similarity	NPC175351
0.8137	Intermediate Similarity	NPC475263
0.8119	Intermediate Similarity	NPC475414
0.8119	Intermediate Similarity	NPC119855
0.8119	Intermediate Similarity	NPC173172
0.8119	Intermediate Similarity	NPC51719
0.8119	Intermediate Similarity	NPC471206
0.8119	Intermediate Similarity	NPC220217
0.8119	Intermediate Similarity	NPC186668
0.8111	Intermediate Similarity	NPC474809
0.8111	Intermediate Similarity	NPC472377
0.8105	Intermediate Similarity	NPC38232
0.81	Intermediate Similarity	NPC45897
0.81	Intermediate Similarity	NPC471938
0.81	Intermediate Similarity	NPC160583
0.81	Intermediate Similarity	NPC474822
0.81	Intermediate Similarity	NPC120321
0.81	Intermediate Similarity	NPC99266
0.81	Intermediate Similarity	NPC473523
0.81	Intermediate Similarity	NPC120009
0.81	Intermediate Similarity	NPC159533
0.8095	Intermediate Similarity	NPC264153
0.809	Intermediate Similarity	NPC142163
0.8085	Intermediate Similarity	NPC220216
0.8081	Intermediate Similarity	NPC198992
0.8081	Intermediate Similarity	NPC471412
0.8081	Intermediate Similarity	NPC268829
0.8081	Intermediate Similarity	NPC295110
0.8081	Intermediate Similarity	NPC25177
0.8081	Intermediate Similarity	NPC222875
0.8081	Intermediate Similarity	NPC247701
0.8077	Intermediate Similarity	NPC470076
0.8068	Intermediate Similarity	NPC242767
0.8065	Intermediate Similarity	NPC472378
0.8065	Intermediate Similarity	NPC104560
0.8061	Intermediate Similarity	NPC316598
0.8061	Intermediate Similarity	NPC247233
0.8058	Intermediate Similarity	NPC475065
0.8046	Intermediate Similarity	NPC189206
0.8043	Intermediate Similarity	NPC474970
0.8043	Intermediate Similarity	NPC471219
0.8041	Intermediate Similarity	NPC154526
0.8041	Intermediate Similarity	NPC190713
0.8041	Intermediate Similarity	NPC472362
0.8041	Intermediate Similarity	NPC472363
0.8039	Intermediate Similarity	NPC329048
0.8039	Intermediate Similarity	NPC330011
0.8039	Intermediate Similarity	NPC472820

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 NPC53555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1376
0.2-0.3	3614
0.3-0.4	2545
0.4-0.5	974
0.5-0.6	261
0.6-0.7	195
0.7-0.8	26
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.883	High Similarity	NPD4225	Approved
0.8163	Intermediate Similarity	NPD7639	Approved
0.8163	Intermediate Similarity	NPD7640	Approved
0.8061	Intermediate Similarity	NPD7638	Approved
0.79	Intermediate Similarity	NPD5344	Discontinued
0.7788	Intermediate Similarity	NPD6686	Approved
0.7706	Intermediate Similarity	NPD7115	Discovery
0.7636	Intermediate Similarity	NPD7328	Approved
0.7636	Intermediate Similarity	NPD7327	Approved
0.7634	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8033	Approved
0.7568	Intermediate Similarity	NPD7516	Approved
0.7547	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD8377	Approved
0.7476	Intermediate Similarity	NPD7632	Discontinued
0.7451	Intermediate Similarity	NPD6648	Approved
0.7434	Intermediate Similarity	NPD8335	Approved
0.7434	Intermediate Similarity	NPD8380	Approved
0.7434	Intermediate Similarity	NPD8379	Approved
0.7434	Intermediate Similarity	NPD8296	Approved
0.7434	Intermediate Similarity	NPD8378	Approved
0.73	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7255	Intermediate Similarity	NPD7902	Approved
0.7216	Intermediate Similarity	NPD7524	Approved
0.7204	Intermediate Similarity	NPD7525	Registered
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7179	Intermediate Similarity	NPD7507	Approved
0.7172	Intermediate Similarity	NPD7838	Discovery
0.7172	Intermediate Similarity	NPD46	Approved
0.7172	Intermediate Similarity	NPD6698	Approved
0.7156	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7503	Approved
0.7103	Intermediate Similarity	NPD7128	Approved
0.7103	Intermediate Similarity	NPD5739	Approved
0.7103	Intermediate Similarity	NPD6675	Approved
0.7103	Intermediate Similarity	NPD6402	Approved
0.71	Intermediate Similarity	NPD7637	Suspended
0.7083	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6051	Approved
0.7027	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD7319	Approved
0.6979	Remote Similarity	NPD6695	Phase 3
0.6972	Remote Similarity	NPD6899	Approved
0.6972	Remote Similarity	NPD6881	Approved
0.6972	Remote Similarity	NPD7320	Approved
0.6961	Remote Similarity	NPD7900	Approved
0.6961	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6933	Approved
0.6939	Remote Similarity	NPD3618	Phase 1
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD6373	Approved
0.6909	Remote Similarity	NPD6372	Approved
0.69	Remote Similarity	NPD5328	Approved
0.6881	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5697	Approved
0.6881	Remote Similarity	NPD5701	Approved
0.6857	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7339	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6848	Remote Similarity	NPD8264	Approved
0.6847	Remote Similarity	NPD7102	Approved
0.6847	Remote Similarity	NPD6883	Approved
0.6847	Remote Similarity	NPD6371	Approved
0.6847	Remote Similarity	NPD7290	Approved
0.6837	Remote Similarity	NPD1694	Approved
0.6832	Remote Similarity	NPD5785	Approved
0.6827	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6011	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8130	Phase 1
0.6786	Remote Similarity	NPD6847	Approved
0.6786	Remote Similarity	NPD6649	Approved
0.6786	Remote Similarity	NPD6650	Approved
0.6786	Remote Similarity	NPD6869	Approved
0.6786	Remote Similarity	NPD6617	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6684	Approved
0.6768	Remote Similarity	NPD7334	Approved
0.6768	Remote Similarity	NPD7146	Approved
0.6768	Remote Similarity	NPD6409	Approved
0.6768	Remote Similarity	NPD5330	Approved
0.6768	Remote Similarity	NPD7521	Approved
0.6765	Remote Similarity	NPD6079	Approved
0.6765	Remote Similarity	NPD8034	Phase 2
0.6765	Remote Similarity	NPD8035	Phase 2
0.6762	Remote Similarity	NPD6084	Phase 2
0.6762	Remote Similarity	NPD6083	Phase 2
0.6757	Remote Similarity	NPD6014	Approved
0.6757	Remote Similarity	NPD6012	Approved
0.6757	Remote Similarity	NPD6013	Approved
0.6739	Remote Similarity	NPD6926	Approved
0.6739	Remote Similarity	NPD6924	Approved
0.6737	Remote Similarity	NPD6929	Approved
0.6735	Remote Similarity	NPD4786	Approved
0.6727	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD6882	Approved
0.6701	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD7750	Discontinued
0.6699	Remote Similarity	NPD4202	Approved
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5737	Approved
0.6634	Remote Similarity	NPD6903	Approved
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6672	Approved
0.6632	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD4755	Approved
0.6602	Remote Similarity	NPD6411	Approved
0.6574	Remote Similarity	NPD4159	Approved
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3133	Approved
0.6566	Remote Similarity	NPD3666	Approved
0.6566	Remote Similarity	NPD3665	Phase 1
0.6545	Remote Similarity	NPD5141	Approved
0.6535	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6925	Approved
0.6526	Remote Similarity	NPD5776	Phase 2
0.6522	Remote Similarity	NPD7152	Approved
0.6522	Remote Similarity	NPD7151	Approved
0.6522	Remote Similarity	NPD7150	Approved
0.6522	Remote Similarity	NPD8133	Approved
0.6509	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5221	Approved
0.6509	Remote Similarity	NPD5222	Approved
0.6509	Remote Similarity	NPD4697	Phase 3
0.6496	Remote Similarity	NPD6009	Approved
0.6495	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD7514	Phase 3
0.6495	Remote Similarity	NPD4819	Approved
0.6495	Remote Similarity	NPD4821	Approved
0.6495	Remote Similarity	NPD7332	Phase 2
0.6495	Remote Similarity	NPD4822	Approved
0.6486	Remote Similarity	NPD6640	Phase 3
0.6486	Remote Similarity	NPD6008	Approved
0.6484	Remote Similarity	NPD6922	Approved
0.6484	Remote Similarity	NPD6923	Approved
0.6481	Remote Similarity	NPD4700	Approved
0.6481	Remote Similarity	NPD4696	Approved
0.6481	Remote Similarity	NPD5286	Approved
0.6481	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD7154	Phase 3
0.6465	Remote Similarity	NPD5362	Discontinued
0.646	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4268	Approved
0.6458	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4271	Approved
0.6458	Remote Similarity	NPD7145	Approved
0.6449	Remote Similarity	NPD5173	Approved
0.6446	Remote Similarity	NPD7604	Phase 2
0.6446	Remote Similarity	NPD8328	Phase 3
0.6442	Remote Similarity	NPD7983	Approved
0.6442	Remote Similarity	NPD5693	Phase 1
0.6442	Remote Similarity	NPD7087	Discontinued
0.6441	Remote Similarity	NPD6335	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD6902	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5223	Approved
0.6417	Remote Similarity	NPD5983	Phase 2
0.6415	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5695	Phase 3
0.6413	Remote Similarity	NPD7143	Approved
0.6413	Remote Similarity	NPD7144	Approved
0.641	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD6274	Approved
0.6408	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7492	Approved
0.6389	Remote Similarity	NPD5696	Approved
0.6387	Remote Similarity	NPD7100	Approved
0.6387	Remote Similarity	NPD7101	Approved
0.6373	Remote Similarity	NPD3573	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6356	Remote Similarity	NPD7505	Discontinued
0.6356	Remote Similarity	NPD6317	Approved
0.6348	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6336	Discontinued
0.6341	Remote Similarity	NPD6616	Approved
0.6337	Remote Similarity	NPD6893	Approved
0.6337	Remote Similarity	NPD5363	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6333	Remote Similarity	NPD6054	Approved
0.6327	Remote Similarity	NPD4695	Discontinued

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