NPASS Compound

Structure

CID31302 OpenBabel06191715362D 33 37 0 0 1 0 0 0 0 0999 V2000 -7.7749 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2880 0.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4017 -0.1754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5342 0.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 2.0475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3966 -0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 -1.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9179 0.6247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 1.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4282 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2575 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9579 0.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9579 3.0212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0825 -1.5733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 2.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2258 -1.3391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 -0.3867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8581 -1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 0.1001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8614 -0.5514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9579 1.0738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2715 1.0738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8012 2.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6128 -0.7567 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8012 1.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5851 -0.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1147 1.5607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4282 -0.3867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2715 0.1001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9090 -0.3489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6444 3.0212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1154 -1.5223 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 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 11 1 1 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 31 2 0 0 0 0 24 26 1 1 0 0 0 24 33 1 0 0 0 0 26 32 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	5.687
LogD:	5.109
LogS:	-5.217
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	4.755
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.087
MDCK Permeability:	1.9553626771084964e-05
Pgp-inhibitor:	0.62
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	92.53714752197266%
Volume Distribution (VD):	1.065
Pgp-substrate:	2.491760730743408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.694
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.814
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	4.699
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.716
Skin Sensitization:	0.901
Carcinogencity:	0.016
Eye Corrosion:	0.674
Eye Irritation:	0.547
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC31302

Natural Product ID:	NPC31302
*Common Name:**	Ocotillone
IUPAC Name:	(5R,8R,9R,10R,13R,14R,17S)-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Ocotillone
Standard InCHIKey:	XSQYWMLMQVUWSF-KATWBKOUSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-22,24,32H,9-18H2,1-8H3/t19-,20+,21+,22-,24-,27+,28-,29-,30+/m1/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@H](C(C)(C)O)O3)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224139
PubChem CID:	12313665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087017]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10896	Juliania adstringens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2555	Dipterus hispidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30306	Dryanobulanops	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10896	Juliania adstringens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12885	Dryanobulanops spp.	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2555	Dipterus hispidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30739	Forsythia suspense	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2633	Baccharis minutiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10896	Juliania adstringens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	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	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[512638]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[512638]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[512638]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[512638]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[512638]
NPT27	Others	Unspecified		IC50	=	64200.0	nM	PMID[512638]

☑ 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 NPC31302 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	337
0.1-0.2	3103
0.2-0.3	12033
0.3-0.4	11948
0.4-0.5	5890
0.5-0.6	6102
0.6-0.7	2712
0.7-0.8	486
0.8-0.85	69
0.85-0.9	11
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245029
0.9481	High Similarity	NPC217559
0.9481	High Similarity	NPC292458
0.9481	High Similarity	NPC268578
0.9125	High Similarity	NPC474448
0.9125	High Similarity	NPC80700
0.8861	High Similarity	NPC242771
0.8861	High Similarity	NPC148740
0.8861	High Similarity	NPC164289
0.8861	High Similarity	NPC102156
0.8861	High Similarity	NPC100366
0.8861	High Similarity	NPC311642
0.8734	High Similarity	NPC77311
0.8659	High Similarity	NPC92139
0.8659	High Similarity	NPC472745
0.8608	High Similarity	NPC472853
0.8554	High Similarity	NPC474174
0.8554	High Similarity	NPC251808
0.8553	High Similarity	NPC472854
0.8519	High Similarity	NPC472744
0.8462	Intermediate Similarity	NPC264602
0.8442	Intermediate Similarity	NPC231680
0.8442	Intermediate Similarity	NPC91387
0.8442	Intermediate Similarity	NPC270306
0.8375	Intermediate Similarity	NPC470609
0.8333	Intermediate Similarity	NPC202937
0.8289	Intermediate Similarity	NPC320549
0.8289	Intermediate Similarity	NPC156277
0.8289	Intermediate Similarity	NPC58057
0.8289	Intermediate Similarity	NPC151018
0.8272	Intermediate Similarity	NPC190940
0.8272	Intermediate Similarity	NPC58631
0.8235	Intermediate Similarity	NPC229407
0.8235	Intermediate Similarity	NPC250687
0.8235	Intermediate Similarity	NPC48824
0.8235	Intermediate Similarity	NPC254572
0.8228	Intermediate Similarity	NPC133596
0.8228	Intermediate Similarity	NPC64081
0.8228	Intermediate Similarity	NPC474574
0.8228	Intermediate Similarity	NPC11907
0.8205	Intermediate Similarity	NPC27349
0.8205	Intermediate Similarity	NPC24014
0.8193	Intermediate Similarity	NPC474996
0.8182	Intermediate Similarity	NPC310766
0.8182	Intermediate Similarity	NPC474123
0.8182	Intermediate Similarity	NPC232112
0.8171	Intermediate Similarity	NPC286719
0.8171	Intermediate Similarity	NPC477936
0.8171	Intermediate Similarity	NPC477286
0.814	Intermediate Similarity	NPC61688
0.814	Intermediate Similarity	NPC269267
0.8133	Intermediate Similarity	NPC473225
0.8125	Intermediate Similarity	NPC476732
0.8125	Intermediate Similarity	NPC199965
0.8077	Intermediate Similarity	NPC254340
0.8072	Intermediate Similarity	NPC269684
0.8072	Intermediate Similarity	NPC259173
0.8072	Intermediate Similarity	NPC111582
0.8072	Intermediate Similarity	NPC477285
0.8052	Intermediate Similarity	NPC469940
0.8052	Intermediate Similarity	NPC197701
0.8026	Intermediate Similarity	NPC324607
0.8026	Intermediate Similarity	NPC131892
0.8026	Intermediate Similarity	NPC213178
0.8026	Intermediate Similarity	NPC321732
0.8026	Intermediate Similarity	NPC327728
0.8026	Intermediate Similarity	NPC6120
0.8025	Intermediate Similarity	NPC81074
0.8025	Intermediate Similarity	NPC80891
0.8025	Intermediate Similarity	NPC201276
0.8025	Intermediate Similarity	NPC477282
0.8	Intermediate Similarity	NPC476727
0.8	Intermediate Similarity	NPC475031
0.8	Intermediate Similarity	NPC477919
0.8	Intermediate Similarity	NPC103782
0.8	Intermediate Similarity	NPC477918
0.8	Intermediate Similarity	NPC23884
0.8	Intermediate Similarity	NPC114378
0.8	Intermediate Similarity	NPC476726
0.8	Intermediate Similarity	NPC474404
0.8	Intermediate Similarity	NPC116683
0.8	Intermediate Similarity	NPC180199
0.8	Intermediate Similarity	NPC476728
0.7978	Intermediate Similarity	NPC206878
0.7978	Intermediate Similarity	NPC470423
0.7976	Intermediate Similarity	NPC473336
0.7976	Intermediate Similarity	NPC471044
0.7975	Intermediate Similarity	NPC195155
0.7975	Intermediate Similarity	NPC174964
0.7975	Intermediate Similarity	NPC97534
0.7975	Intermediate Similarity	NPC273366
0.7975	Intermediate Similarity	NPC125767
0.7975	Intermediate Similarity	NPC159789
0.7975	Intermediate Similarity	NPC21220
0.7955	Intermediate Similarity	NPC471747
0.7952	Intermediate Similarity	NPC317066
0.7952	Intermediate Similarity	NPC121121
0.7952	Intermediate Similarity	NPC24556
0.7952	Intermediate Similarity	NPC477935
0.7922	Intermediate Similarity	NPC477929
0.7907	Intermediate Similarity	NPC263802
0.7901	Intermediate Similarity	NPC34046
0.7901	Intermediate Similarity	NPC324700
0.7901	Intermediate Similarity	NPC171426
0.7901	Intermediate Similarity	NPC80089
0.7901	Intermediate Similarity	NPC224802
0.7875	Intermediate Similarity	NPC472487
0.7875	Intermediate Similarity	NPC5767
0.7875	Intermediate Similarity	NPC472486
0.7875	Intermediate Similarity	NPC475742
0.7849	Intermediate Similarity	NPC178853
0.7848	Intermediate Similarity	NPC280026
0.7848	Intermediate Similarity	NPC167702
0.7831	Intermediate Similarity	NPC12933
0.7831	Intermediate Similarity	NPC469745
0.7821	Intermediate Similarity	NPC473267
0.7821	Intermediate Similarity	NPC89310
0.7816	Intermediate Similarity	NPC56777
0.7816	Intermediate Similarity	NPC201607
0.7792	Intermediate Similarity	NPC476734
0.7792	Intermediate Similarity	NPC469941
0.7792	Intermediate Similarity	NPC252032
0.7792	Intermediate Similarity	NPC319671
0.7791	Intermediate Similarity	NPC477283
0.7791	Intermediate Similarity	NPC155531
0.7791	Intermediate Similarity	NPC472272
0.7791	Intermediate Similarity	NPC215968
0.7778	Intermediate Similarity	NPC221420
0.7778	Intermediate Similarity	NPC470424
0.7765	Intermediate Similarity	NPC50438
0.775	Intermediate Similarity	NPC212733
0.775	Intermediate Similarity	NPC477934
0.7738	Intermediate Similarity	NPC268040
0.7738	Intermediate Similarity	NPC61107
0.7738	Intermediate Similarity	NPC475388
0.7738	Intermediate Similarity	NPC289486
0.7722	Intermediate Similarity	NPC81759
0.7711	Intermediate Similarity	NPC261616
0.7701	Intermediate Similarity	NPC469322
0.7692	Intermediate Similarity	NPC476731
0.7692	Intermediate Similarity	NPC215570
0.7692	Intermediate Similarity	NPC108131
0.7683	Intermediate Similarity	NPC185465
0.7667	Intermediate Similarity	NPC161035
0.7654	Intermediate Similarity	NPC4209
0.7654	Intermediate Similarity	NPC477932
0.7654	Intermediate Similarity	NPC477933
0.7647	Intermediate Similarity	NPC470070
0.764	Intermediate Similarity	NPC185529
0.764	Intermediate Similarity	NPC475056
0.764	Intermediate Similarity	NPC472146
0.7632	Intermediate Similarity	NPC42060
0.7625	Intermediate Similarity	NPC472945
0.7625	Intermediate Similarity	NPC472944
0.7625	Intermediate Similarity	NPC133922
0.7619	Intermediate Similarity	NPC50658
0.7614	Intermediate Similarity	NPC255176
0.7614	Intermediate Similarity	NPC476435
0.7595	Intermediate Similarity	NPC8004
0.7595	Intermediate Similarity	NPC131506
0.7595	Intermediate Similarity	NPC127283
0.7595	Intermediate Similarity	NPC157777
0.759	Intermediate Similarity	NPC477287
0.759	Intermediate Similarity	NPC320144
0.7564	Intermediate Similarity	NPC196197
0.7564	Intermediate Similarity	NPC64466
0.7564	Intermediate Similarity	NPC474962
0.7561	Intermediate Similarity	NPC317913
0.7561	Intermediate Similarity	NPC207010
0.7561	Intermediate Similarity	NPC212453
0.7561	Intermediate Similarity	NPC298168
0.7561	Intermediate Similarity	NPC143133
0.7561	Intermediate Similarity	NPC171658
0.7558	Intermediate Similarity	NPC291310
0.7558	Intermediate Similarity	NPC319909
0.7556	Intermediate Similarity	NPC262870
0.7531	Intermediate Similarity	NPC472311
0.7529	Intermediate Similarity	NPC13494
0.7529	Intermediate Similarity	NPC145143
0.7529	Intermediate Similarity	NPC154043
0.7529	Intermediate Similarity	NPC328007
0.7529	Intermediate Similarity	NPC202688
0.7529	Intermediate Similarity	NPC60018
0.7528	Intermediate Similarity	NPC24705
0.7528	Intermediate Similarity	NPC200580
0.7528	Intermediate Similarity	NPC56962
0.75	Intermediate Similarity	NPC477851
0.75	Intermediate Similarity	NPC16449
0.75	Intermediate Similarity	NPC305808
0.75	Intermediate Similarity	NPC475943
0.75	Intermediate Similarity	NPC17336
0.75	Intermediate Similarity	NPC153719
0.75	Intermediate Similarity	NPC472341
0.75	Intermediate Similarity	NPC239938
0.75	Intermediate Similarity	NPC243469
0.75	Intermediate Similarity	NPC190827
0.75	Intermediate Similarity	NPC473238
0.7474	Intermediate Similarity	NPC477172
0.747	Intermediate Similarity	NPC471045
0.747	Intermediate Similarity	NPC329117

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 NPC31302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	3460
0.2-0.3	3707
0.3-0.4	971
0.4-0.5	251
0.5-0.6	269
0.6-0.7	90
0.7-0.8	18
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8289	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4245	Approved
0.8158	Intermediate Similarity	NPD4789	Approved
0.8158	Intermediate Similarity	NPD4244	Approved
0.8133	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5360	Phase 3
0.8026	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3698	Phase 2
0.7975	Intermediate Similarity	NPD3703	Phase 2
0.7973	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6114	Approved
0.7901	Intermediate Similarity	NPD6115	Approved
0.7901	Intermediate Similarity	NPD6697	Approved
0.7901	Intermediate Similarity	NPD6118	Approved
0.7848	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5777	Approved
0.775	Intermediate Similarity	NPD3702	Approved
0.7654	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD4224	Phase 2
0.7595	Intermediate Similarity	NPD4758	Discontinued
0.7595	Intermediate Similarity	NPD6081	Approved
0.7561	Intermediate Similarity	NPD6116	Phase 1
0.7423	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3671	Phase 1
0.7262	Intermediate Similarity	NPD5364	Discontinued
0.7241	Intermediate Similarity	NPD4788	Approved
0.7093	Intermediate Similarity	NPD6928	Phase 2
0.6966	Remote Similarity	NPD4786	Approved
0.6889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4787	Phase 1
0.6809	Remote Similarity	NPD8034	Phase 2
0.6809	Remote Similarity	NPD8035	Phase 2
0.6742	Remote Similarity	NPD3667	Approved
0.6737	Remote Similarity	NPD8171	Discontinued
0.6737	Remote Similarity	NPD6399	Phase 3
0.6602	Remote Similarity	NPD6412	Phase 2
0.6596	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD3133	Approved
0.6593	Remote Similarity	NPD3665	Phase 1
0.6556	Remote Similarity	NPD4221	Approved
0.6556	Remote Similarity	NPD4223	Phase 3
0.6522	Remote Similarity	NPD5329	Approved
0.6489	Remote Similarity	NPD6903	Approved
0.6489	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3617	Approved
0.6465	Remote Similarity	NPD6083	Phase 2
0.6465	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD7521	Approved
0.6452	Remote Similarity	NPD7334	Approved
0.6452	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD5330	Approved
0.6452	Remote Similarity	NPD6684	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD7146	Approved
0.6444	Remote Similarity	NPD4139	Approved
0.6444	Remote Similarity	NPD4692	Approved
0.6436	Remote Similarity	NPD1700	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.6413	Remote Similarity	NPD4197	Approved
0.6392	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD8133	Approved
0.6346	Remote Similarity	NPD6920	Discontinued
0.6339	Remote Similarity	NPD6059	Approved
0.6339	Remote Similarity	NPD6054	Approved
0.6337	Remote Similarity	NPD8418	Phase 2
0.6316	Remote Similarity	NPD6672	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD4802	Phase 2
0.6292	Remote Similarity	NPD4238	Approved
0.6277	Remote Similarity	NPD4688	Approved
0.6277	Remote Similarity	NPD4690	Approved
0.6277	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD6098	Approved
0.6277	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD5205	Approved
0.6277	Remote Similarity	NPD4138	Approved
0.6277	Remote Similarity	NPD4689	Approved
0.6273	Remote Similarity	NPD6940	Discontinued
0.6263	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5695	Phase 3
0.6239	Remote Similarity	NPD4632	Approved
0.6238	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD7638	Approved
0.6237	Remote Similarity	NPD3668	Phase 3
0.6228	Remote Similarity	NPD6370	Approved
0.6226	Remote Similarity	NPD7320	Approved
0.6226	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7524	Approved
0.6203	Remote Similarity	NPD3198	Approved
0.619	Remote Similarity	NPD6008	Approved
0.619	Remote Similarity	NPD7128	Approved
0.619	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6675	Approved
0.619	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD7639	Approved
0.6176	Remote Similarity	NPD7640	Approved
0.6162	Remote Similarity	NPD7748	Approved
0.6154	Remote Similarity	NPD7525	Registered
0.6147	Remote Similarity	NPD8297	Approved
0.614	Remote Similarity	NPD6016	Approved
0.614	Remote Similarity	NPD6015	Approved
0.6139	Remote Similarity	NPD4755	Approved
0.6121	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD4634	Approved
0.6105	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5690	Phase 2
0.6105	Remote Similarity	NPD4694	Approved
0.6105	Remote Similarity	NPD5280	Approved
0.6102	Remote Similarity	NPD7736	Approved
0.61	Remote Similarity	NPD4629	Approved
0.61	Remote Similarity	NPD5210	Approved
0.6098	Remote Similarity	NPD371	Approved
0.6087	Remote Similarity	NPD5988	Approved
0.6082	Remote Similarity	NPD6904	Approved
0.6082	Remote Similarity	NPD6673	Approved
0.6082	Remote Similarity	NPD6080	Approved
0.6075	Remote Similarity	NPD6415	Discontinued
0.6075	Remote Similarity	NPD6899	Approved
0.6075	Remote Similarity	NPD6881	Approved
0.6071	Remote Similarity	NPD7115	Discovery
0.6068	Remote Similarity	NPD6616	Approved
0.6068	Remote Similarity	NPD7507	Approved
0.6067	Remote Similarity	NPD6933	Approved
0.6058	Remote Similarity	NPD7632	Discontinued
0.6053	Remote Similarity	NPD6319	Approved
0.604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4697	Phase 3
0.604	Remote Similarity	NPD5222	Approved
0.604	Remote Similarity	NPD5221	Approved
0.602	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD4700	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD5285	Approved
0.6019	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4696	Approved
0.6019	Remote Similarity	NPD5286	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6019	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8293	Discontinued
0.6017	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6705	Phase 1
0.6	Remote Similarity	NPD6001	Approved
0.5981	Remote Similarity	NPD5701	Approved
0.5981	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD7902	Approved
0.598	Remote Similarity	NPD5173	Approved
0.5979	Remote Similarity	NPD5208	Approved
0.5966	Remote Similarity	NPD6033	Approved
0.5963	Remote Similarity	NPD7102	Approved
0.5963	Remote Similarity	NPD7290	Approved
0.5963	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD5223	Approved
0.596	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD3669	Approved
0.5957	Remote Similarity	NPD6695	Phase 3
0.5957	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7339	Approved
0.5955	Remote Similarity	NPD6942	Approved
0.5941	Remote Similarity	NPD7991	Discontinued
0.5929	Remote Similarity	NPD6009	Approved
0.5926	Remote Similarity	NPD6011	Approved
0.5926	Remote Similarity	NPD6686	Approved
0.5917	Remote Similarity	NPD7319	Approved
0.5914	Remote Similarity	NPD1779	Approved
0.5914	Remote Similarity	NPD1780	Approved
0.5909	Remote Similarity	NPD6650	Approved
0.5909	Remote Similarity	NPD8130	Phase 1
0.5909	Remote Similarity	NPD6617	Approved
0.5909	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD6649	Approved
0.5909	Remote Similarity	NPD6869	Approved
0.5905	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD5224	Approved
0.5905	Remote Similarity	NPD5211	Phase 2
0.5905	Remote Similarity	NPD5225	Approved
0.5905	Remote Similarity	NPD5226	Approved
0.5904	Remote Similarity	NPD7909	Approved
0.5897	Remote Similarity	NPD6067	Discontinued
0.5897	Remote Similarity	NPD7604	Phase 2
0.5895	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD6013	Approved
0.5872	Remote Similarity	NPD6012	Approved
0.587	Remote Similarity	NPD4195	Approved
0.5862	Remote Similarity	NPD5983	Phase 2
0.5856	Remote Similarity	NPD6882	Approved
0.5849	Remote Similarity	NPD4754	Approved
0.5849	Remote Similarity	NPD5174	Approved
0.5849	Remote Similarity	NPD5175	Approved
0.5843	Remote Similarity	NPD6924	Approved
0.5843	Remote Similarity	NPD6926	Approved
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6930	Phase 2
0.5806	Remote Similarity	NPD6931	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