NPASS Compound

Structure

NPC329997 OpenBabel07101719252D 48 50 0 0 1 0 0 0 0 0999 V2000 -3.8927 -5.8178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5869 -5.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6237 2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3179 2.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3179 -2.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4769 -3.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 -3.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3192 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3192 -3.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4531 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4531 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4280 -4.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1100 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6359 -5.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3669 2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2690 -2.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8224 -4.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5871 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5871 -3.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -3.2653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1711 -3.5014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9021 0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0121 -2.2142 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5352 -1.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7211 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 -1.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4158 -1.9563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1230 -2.4563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1314 -5.3753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7211 -3.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1222 -3.8104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 0.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7211 -0.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5474 -0.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4103 -1.8518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -2.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 -0.9271 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 2.8551 -2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 -4.2164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9632 -2.5232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 18 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 27 1 0 0 0 0 14 25 1 0 0 0 0 14 33 1 0 0 0 0 15 22 1 0 0 0 0 15 43 1 0 0 0 0 16 22 2 0 0 0 0 16 44 1 0 0 0 0 17 34 1 0 0 0 0 17 45 1 0 0 0 0 20 28 1 0 0 0 0 21 35 2 0 0 0 0 21 46 1 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 36 1 0 0 0 0 25 34 1 1 0 0 0 25 46 1 0 0 0 0 26 37 2 0 0 0 0 26 47 1 0 0 0 0 27 38 2 0 0 0 0 27 48 1 0 0 0 0 28 31 1 0 0 0 0 28 47 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 6 0 0 0 29 34 1 0 0 0 0 30 39 2 0 0 0 0 30 45 1 0 0 0 0 31 40 2 0 0 0 0 31 43 1 0 0 0 0 32 44 1 0 0 0 0 32 48 1 1 0 0 0 33 41 1 1 0 0 0 34 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	678.29
Volume:	670.286
LogP:	4.504
LogD:	2.674
LogS:	-4.518
# Rotatable Bonds:	19
TPSA:	201.42
# H-Bond Aceptor:	14
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	5.022
Fsp3:	0.618
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978
MDCK Permeability:	5.062007767264731e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.375
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.787
Plasma Protein Binding (PPB):	84.81098175048828%
Volume Distribution (VD):	0.883
Pgp-substrate:	12.415767669677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.828
CYP2C9-substrate:	0.31
CYP2D6-inhibitor:	0.121
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	4.991
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.938
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.476
Skin Sensitization:	0.26
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.122
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC329997

Natural Product ID:	NPC329997
*Common Name:**	Jatamanvaltrate D
IUPAC Name:	[(1S,4aR,6S,7R,7aS)-6-acetyloxy-4a,7-dihydroxy-1-(3-methylbutanoyloxy)-4-[[3-methyl-2-(3-methylbutanoyloxy)butanoyl]oxymethyl]-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 2-hydroxybenzoate
Synonyms:	Jatamanvaltrate D
Standard InCHIKey:	UWCWLUDDBLLVGQ-MKIXRFLUSA-N
Standard InCHI:	InChI=1S/C34H46O14/c1-18(2)12-26(37)47-28(20(5)6)31(40)43-15-22-16-44-32(48-27(38)13-19(3)4)29-33(22,41)14-25(46-21(7)35)34(29,42)17-45-30(39)23-10-8-9-11-24(23)36/h8-11,16,18-20,25,28-29,32,36,41-42H,12-15,17H2,1-7H3/t25-,28?,29-,32-,33-,34+/m0/s1
SMILES:	CC(CC(=O)O[C@@H]1OC=C([C@@]2([C@H]1[C@@](O)(COC(=O)c1ccccc1O)[C@H](C2)OC(=O)C)O)COC(=O)C(C(C)C)OC(=O)CC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553189
PubChem CID:	42640647
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[555546]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	4500.0	nM	PMID[555546]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	9700.0	nM	PMID[555546]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3800.0	nM	PMID[555546]

☑ 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 NPC329997 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	336
0.1-0.2	1269
0.2-0.3	2880
0.3-0.4	6892
0.4-0.5	10910
0.5-0.6	7131
0.6-0.7	10338
0.7-0.8	2867
0.8-0.85	65
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9267	High Similarity	NPC189631
0.8718	High Similarity	NPC289021
0.8718	High Similarity	NPC158546
0.8684	High Similarity	NPC186296
0.859	High Similarity	NPC478236
0.859	High Similarity	NPC478234
0.8553	High Similarity	NPC154262
0.8553	High Similarity	NPC159387
0.8553	High Similarity	NPC7518
0.8553	High Similarity	NPC137501
0.8544	High Similarity	NPC194705
0.8535	High Similarity	NPC240592
0.8535	High Similarity	NPC117346
0.8506	High Similarity	NPC184464
0.8506	High Similarity	NPC251062
0.8491	Intermediate Similarity	NPC229354
0.8471	Intermediate Similarity	NPC96599
0.8447	Intermediate Similarity	NPC475378
0.8428	Intermediate Similarity	NPC478235
0.8387	Intermediate Similarity	NPC202391
0.8387	Intermediate Similarity	NPC296659
0.8365	Intermediate Similarity	NPC475407
0.8364	Intermediate Similarity	NPC109990
0.8323	Intermediate Similarity	NPC478232
0.8303	Intermediate Similarity	NPC145847
0.8293	Intermediate Similarity	NPC208676
0.8293	Intermediate Similarity	NPC130489
0.8289	Intermediate Similarity	NPC27721
0.8258	Intermediate Similarity	NPC45307
0.825	Intermediate Similarity	NPC475379
0.8247	Intermediate Similarity	NPC475413
0.8247	Intermediate Similarity	NPC474303
0.8239	Intermediate Similarity	NPC161955
0.8224	Intermediate Similarity	NPC202729
0.8217	Intermediate Similarity	NPC170668
0.821	Intermediate Similarity	NPC472127
0.821	Intermediate Similarity	NPC472128
0.8182	Intermediate Similarity	NPC138993
0.8182	Intermediate Similarity	NPC49597
0.8171	Intermediate Similarity	NPC478226
0.8166	Intermediate Similarity	NPC21956
0.8165	Intermediate Similarity	NPC205389
0.816	Intermediate Similarity	NPC475484
0.8158	Intermediate Similarity	NPC79699
0.8153	Intermediate Similarity	NPC77922
0.8153	Intermediate Similarity	NPC473281
0.8148	Intermediate Similarity	NPC183536
0.8148	Intermediate Similarity	NPC34965
0.8137	Intermediate Similarity	NPC474620
0.8129	Intermediate Similarity	NPC473497
0.8117	Intermediate Similarity	NPC473301
0.8117	Intermediate Similarity	NPC475195
0.8095	Intermediate Similarity	NPC294722
0.8092	Intermediate Similarity	NPC136608
0.8092	Intermediate Similarity	NPC38420
0.8092	Intermediate Similarity	NPC28836
0.8092	Intermediate Similarity	NPC311492
0.8089	Intermediate Similarity	NPC237872
0.8089	Intermediate Similarity	NPC88754
0.8089	Intermediate Similarity	NPC263397
0.8089	Intermediate Similarity	NPC302286
0.8089	Intermediate Similarity	NPC116104
0.8084	Intermediate Similarity	NPC476011
0.8079	Intermediate Similarity	NPC233860
0.8077	Intermediate Similarity	NPC46644
0.8075	Intermediate Similarity	NPC35097
0.8072	Intermediate Similarity	NPC474936
0.8063	Intermediate Similarity	NPC25484
0.8063	Intermediate Similarity	NPC232583
0.8063	Intermediate Similarity	NPC477097
0.8063	Intermediate Similarity	NPC477101
0.8063	Intermediate Similarity	NPC477099
0.8061	Intermediate Similarity	NPC187205
0.805	Intermediate Similarity	NPC474268
0.805	Intermediate Similarity	NPC119773
0.805	Intermediate Similarity	NPC473147
0.805	Intermediate Similarity	NPC143246
0.805	Intermediate Similarity	NPC475539
0.8049	Intermediate Similarity	NPC472890
0.8049	Intermediate Similarity	NPC478221
0.8047	Intermediate Similarity	NPC301910
0.8047	Intermediate Similarity	NPC130730
0.8038	Intermediate Similarity	NPC122491
0.8038	Intermediate Similarity	NPC32
0.8038	Intermediate Similarity	NPC194938
0.8037	Intermediate Similarity	NPC257847
0.8026	Intermediate Similarity	NPC472248
0.8025	Intermediate Similarity	NPC477100
0.8025	Intermediate Similarity	NPC477098
0.8024	Intermediate Similarity	NPC317544
0.8023	Intermediate Similarity	NPC195972
0.8013	Intermediate Similarity	NPC242355
0.8012	Intermediate Similarity	NPC22137
0.8012	Intermediate Similarity	NPC179914
0.8011	Intermediate Similarity	NPC106700
0.8	Intermediate Similarity	NPC272523
0.8	Intermediate Similarity	NPC473149
0.8	Intermediate Similarity	NPC325805
0.8	Intermediate Similarity	NPC272550
0.7988	Intermediate Similarity	NPC475979
0.7988	Intermediate Similarity	NPC72016
0.7987	Intermediate Similarity	NPC210330
0.7987	Intermediate Similarity	NPC475528
0.7976	Intermediate Similarity	NPC206815
0.7965	Intermediate Similarity	NPC222665
0.7965	Intermediate Similarity	NPC271755
0.7965	Intermediate Similarity	NPC149502
0.7965	Intermediate Similarity	NPC183441
0.7965	Intermediate Similarity	NPC254071
0.7961	Intermediate Similarity	NPC239358
0.7961	Intermediate Similarity	NPC233692
0.7952	Intermediate Similarity	NPC29552
0.7952	Intermediate Similarity	NPC478225
0.7952	Intermediate Similarity	NPC472889
0.795	Intermediate Similarity	NPC83975
0.795	Intermediate Similarity	NPC120728
0.7939	Intermediate Similarity	NPC208173
0.7939	Intermediate Similarity	NPC478230
0.7939	Intermediate Similarity	NPC69043
0.7939	Intermediate Similarity	NPC170189
0.7937	Intermediate Similarity	NPC37838
0.7935	Intermediate Similarity	NPC86772
0.7929	Intermediate Similarity	NPC91288
0.7929	Intermediate Similarity	NPC121703
0.7927	Intermediate Similarity	NPC76041
0.7927	Intermediate Similarity	NPC184284
0.7925	Intermediate Similarity	NPC478240
0.7925	Intermediate Similarity	NPC63304
0.7922	Intermediate Similarity	NPC200154
0.7921	Intermediate Similarity	NPC282636
0.7921	Intermediate Similarity	NPC294863
0.7917	Intermediate Similarity	NPC224530
0.7917	Intermediate Similarity	NPC129217
0.7917	Intermediate Similarity	NPC216496
0.7917	Intermediate Similarity	NPC85707
0.7917	Intermediate Similarity	NPC159579
0.7917	Intermediate Similarity	NPC259957
0.7917	Intermediate Similarity	NPC48093
0.7914	Intermediate Similarity	NPC131874
0.7914	Intermediate Similarity	NPC473966
0.7907	Intermediate Similarity	NPC472159
0.7907	Intermediate Similarity	NPC277532
0.7907	Intermediate Similarity	NPC209550
0.7907	Intermediate Similarity	NPC138990
0.7907	Intermediate Similarity	NPC175429
0.7904	Intermediate Similarity	NPC104677
0.7888	Intermediate Similarity	NPC120536
0.7879	Intermediate Similarity	NPC470331
0.7879	Intermediate Similarity	NPC185103
0.7879	Intermediate Similarity	NPC198236
0.7879	Intermediate Similarity	NPC478231
0.7879	Intermediate Similarity	NPC137301
0.7874	Intermediate Similarity	NPC472158
0.7871	Intermediate Similarity	NPC285221
0.7871	Intermediate Similarity	NPC194769
0.787	Intermediate Similarity	NPC150164
0.787	Intermediate Similarity	NPC27942
0.7866	Intermediate Similarity	NPC190217
0.7862	Intermediate Similarity	NPC478250
0.7862	Intermediate Similarity	NPC293154
0.7861	Intermediate Similarity	NPC101399
0.7861	Intermediate Similarity	NPC217822
0.7861	Intermediate Similarity	NPC11847
0.7861	Intermediate Similarity	NPC474522
0.7861	Intermediate Similarity	NPC13989
0.7861	Intermediate Similarity	NPC221288
0.7857	Intermediate Similarity	NPC470143
0.7857	Intermediate Similarity	NPC322503
0.7857	Intermediate Similarity	NPC472250
0.7857	Intermediate Similarity	NPC153617
0.7853	Intermediate Similarity	NPC147224
0.7853	Intermediate Similarity	NPC186746
0.7853	Intermediate Similarity	NPC162569
0.7853	Intermediate Similarity	NPC35160
0.7849	Intermediate Similarity	NPC5319
0.7848	Intermediate Similarity	NPC469911
0.7844	Intermediate Similarity	NPC43638
0.7844	Intermediate Similarity	NPC476026
0.7844	Intermediate Similarity	NPC474398
0.7844	Intermediate Similarity	NPC474401
0.7844	Intermediate Similarity	NPC474441
0.7844	Intermediate Similarity	NPC288084
0.7843	Intermediate Similarity	NPC475569
0.784	Intermediate Similarity	NPC302989
0.7836	Intermediate Similarity	NPC282551
0.7836	Intermediate Similarity	NPC64425
0.7834	Intermediate Similarity	NPC31745
0.7834	Intermediate Similarity	NPC475660
0.7834	Intermediate Similarity	NPC220936
0.7831	Intermediate Similarity	NPC317585
0.7829	Intermediate Similarity	NPC176246
0.7826	Intermediate Similarity	NPC212808
0.7824	Intermediate Similarity	NPC475183
0.7824	Intermediate Similarity	NPC66087
0.7824	Intermediate Similarity	NPC183672
0.7824	Intermediate Similarity	NPC278419
0.7824	Intermediate Similarity	NPC179198
0.7824	Intermediate Similarity	NPC471286
0.7824	Intermediate Similarity	NPC161151
0.7821	Intermediate Similarity	NPC471345

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 NPC329997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	807
0.2-0.3	1795
0.3-0.4	2727
0.4-0.5	2138
0.5-0.6	1025
0.6-0.7	334
0.7-0.8	43
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
0.8023	Intermediate Similarity	NPD7685	Pre-registration
0.7849	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7075	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7799	Discontinued
0.7622	Intermediate Similarity	NPD5403	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.756	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7515	Intermediate Similarity	NPD5402	Approved
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7486	Intermediate Similarity	NPD3818	Discontinued
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6797	Phase 2
0.7452	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6799	Approved
0.7416	Intermediate Similarity	NPD6559	Discontinued
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7381	Intermediate Similarity	NPD4380	Phase 2
0.7381	Intermediate Similarity	NPD6599	Discontinued
0.7348	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7054	Approved
0.731	Intermediate Similarity	NPD3817	Phase 2
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD7074	Phase 3
0.7303	Intermediate Similarity	NPD7472	Approved
0.729	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5763	Approved
0.7284	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6004	Phase 3
0.7284	Intermediate Similarity	NPD5762	Approved
0.7284	Intermediate Similarity	NPD6002	Phase 3
0.7284	Intermediate Similarity	NPD6005	Phase 3
0.7277	Intermediate Similarity	NPD8320	Phase 1
0.7277	Intermediate Similarity	NPD8319	Approved
0.7248	Intermediate Similarity	NPD9493	Approved
0.7239	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7186	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7168	Intermediate Similarity	NPD7768	Phase 2
0.7168	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7151	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD6653	Approved
0.7117	Intermediate Similarity	NPD1551	Phase 2
0.711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7266	Discontinued
0.707	Intermediate Similarity	NPD5647	Approved
0.7066	Intermediate Similarity	NPD7236	Approved
0.7055	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7043	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD9717	Approved
0.7027	Intermediate Similarity	NPD8434	Phase 2
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD1203	Approved
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6994	Remote Similarity	NPD1934	Approved
0.6989	Remote Similarity	NPD6234	Discontinued
0.6984	Remote Similarity	NPD6535	Approved
0.6984	Remote Similarity	NPD6534	Approved
0.6983	Remote Similarity	NPD6166	Phase 2
0.6983	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2532	Approved
0.6982	Remote Similarity	NPD2533	Approved
0.6982	Remote Similarity	NPD2534	Approved
0.6979	Remote Similarity	NPD6778	Approved
0.6979	Remote Similarity	NPD6779	Approved
0.6979	Remote Similarity	NPD6780	Approved
0.6979	Remote Similarity	NPD6776	Approved
0.6979	Remote Similarity	NPD6782	Approved
0.6979	Remote Similarity	NPD6781	Approved
0.6979	Remote Similarity	NPD6777	Approved
0.6975	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD447	Suspended
0.6971	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7696	Phase 3
0.6959	Remote Similarity	NPD7239	Suspended
0.6959	Remote Similarity	NPD7698	Approved
0.6959	Remote Similarity	NPD7697	Approved
0.6954	Remote Similarity	NPD5760	Phase 2
0.6954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5761	Phase 2
0.6951	Remote Similarity	NPD2799	Discontinued
0.695	Remote Similarity	NPD7930	Approved
0.6946	Remote Similarity	NPD3750	Approved
0.6946	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7473	Discontinued
0.6936	Remote Similarity	NPD7411	Suspended
0.6928	Remote Similarity	NPD9545	Approved
0.6928	Remote Similarity	NPD1549	Phase 2
0.6923	Remote Similarity	NPD7870	Phase 2
0.6923	Remote Similarity	NPD7871	Phase 2
0.6914	Remote Similarity	NPD1240	Approved
0.6909	Remote Similarity	NPD2796	Approved
0.6906	Remote Similarity	NPD7228	Approved
0.6904	Remote Similarity	NPD7701	Phase 2
0.6899	Remote Similarity	NPD2797	Approved
0.6897	Remote Similarity	NPD37	Approved
0.6894	Remote Similarity	NPD2313	Discontinued
0.6894	Remote Similarity	NPD6798	Discontinued
0.689	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7801	Approved
0.6882	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4965	Approved
0.6875	Remote Similarity	NPD4967	Phase 2
0.6875	Remote Similarity	NPD4966	Approved
0.6872	Remote Similarity	NPD6232	Discontinued
0.6871	Remote Similarity	NPD230	Phase 1
0.6867	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1653	Approved
0.6859	Remote Similarity	NPD1091	Approved
0.6857	Remote Similarity	NPD2801	Approved
0.6848	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD1512	Approved
0.6829	Remote Similarity	NPD1607	Approved
0.6824	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3226	Approved
0.6821	Remote Similarity	NPD6823	Phase 2
0.6816	Remote Similarity	NPD8127	Discontinued
0.6813	Remote Similarity	NPD3751	Discontinued
0.6802	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD919	Approved
0.6793	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6362	Approved
0.679	Remote Similarity	NPD3268	Approved
0.6786	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6764	Approved
0.6757	Remote Similarity	NPD8368	Discontinued
0.6757	Remote Similarity	NPD6765	Approved
0.675	Remote Similarity	NPD1019	Discontinued
0.6748	Remote Similarity	NPD6233	Phase 2
0.6748	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6273	Approved
0.6742	Remote Similarity	NPD3749	Approved
0.6738	Remote Similarity	NPD8407	Phase 2
0.6728	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1511	Approved
0.6716	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7783	Phase 2
0.6711	Remote Similarity	NPD9266	Approved
0.6711	Remote Similarity	NPD74	Approved
0.6707	Remote Similarity	NPD4060	Phase 1
0.6705	Remote Similarity	NPD920	Approved
0.6704	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.67	Remote Similarity	NPD8151	Discontinued
0.6687	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1164	Approved
0.6687	Remote Similarity	NPD411	Approved
0.6685	Remote Similarity	NPD3787	Discontinued
0.6683	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD6663	Approved
0.6644	Remote Similarity	NPD9264	Approved
0.6644	Remote Similarity	NPD9267	Approved
0.6644	Remote Similarity	NPD9263	Approved
0.6629	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5958	Discontinued
0.6627	Remote Similarity	NPD6651	Approved
0.6614	Remote Similarity	NPD6785	Approved
0.6614	Remote Similarity	NPD6784	Approved
0.6607	Remote Similarity	NPD5405	Approved
0.6607	Remote Similarity	NPD5406	Approved
0.6607	Remote Similarity	NPD5408	Approved
0.6607	Remote Similarity	NPD5404	Approved
0.6606	Remote Similarity	NPD4307	Phase 2
0.6605	Remote Similarity	NPD5736	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