NPASS Compound

Structure

NPC307167 OpenBabel07101719132D 56 62 0 0 1 0 0 0 0 0999 V2000 -11.9878 -1.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8583 1.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3662 0.7251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4275 -0.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5506 0.2695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3173 2.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4437 -0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3173 -1.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9278 0.6314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2817 -1.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0218 3.0536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0833 -1.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1696 2.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2604 -1.3535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8673 -1.3355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4650 1.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1696 -0.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5787 2.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1355 -1.8670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8814 -0.5573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6127 1.0853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0218 0.1012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5787 1.5774 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3173 1.0853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8741 2.5615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6193 -0.7648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6127 0.1012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1355 -2.8512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4310 1.0853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2832 -3.3432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4310 0.1012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4310 -2.8512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5787 -0.3908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0218 1.0853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4310 -1.8670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7264 0.1012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8741 1.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6021 -0.7133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1696 1.5774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4650 -0.3908 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3173 0.1012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9188 -0.3527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4310 3.0536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7605 1.5774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7264 3.0536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9878 -3.3432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2832 1.5774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2832 -4.3274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2832 -0.3908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5787 -3.3432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1381 -1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2832 -1.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8741 -0.3908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7264 1.0853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5787 -1.3750 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 37 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 7 40 1 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 26 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 42 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 41 1 0 0 0 0 18 43 1 0 0 0 0 19 1 1 6 0 0 0 19 28 1 0 0 0 0 19 52 1 0 0 0 0 20 10 1 1 0 0 0 20 27 1 0 0 0 0 20 42 1 0 0 0 0 21 27 1 0 0 0 0 21 44 1 1 0 0 0 22 34 1 0 0 0 0 22 53 1 6 0 0 0 23 18 1 1 0 0 0 23 29 1 0 0 0 0 23 54 1 0 0 0 0 24 39 1 1 0 0 0 24 41 1 0 0 0 0 25 37 1 0 0 0 0 25 45 1 1 0 0 0 26 38 1 6 0 0 0 26 56 1 0 0 0 0 27 40 1 6 0 0 0 28 30 1 0 0 0 0 28 46 1 1 0 0 0 29 31 1 0 0 0 0 29 47 1 6 0 0 0 30 32 1 0 0 0 0 30 48 1 6 0 0 0 31 33 1 0 0 0 0 31 49 1 1 0 0 0 32 35 1 0 0 0 0 32 50 1 6 0 0 0 33 36 1 0 0 0 0 33 55 1 6 0 0 0 34 37 1 0 0 0 0 34 39 1 1 0 0 0 35 52 1 0 0 0 0 35 55 1 1 0 0 0 36 53 1 1 0 0 0 36 54 1 0 0 0 0 38 51 1 0 0 0 0 39 6 1 1 0 0 0 40 41 1 1 0 0 0 41 8 1 1 0 0 0 42 9 1 6 0 0 0 42 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	800.49
Volume:	798.156
LogP:	3.095
LogD:	3.509
LogS:	-3.346
# Rotatable Bonds:	7
TPSA:	228.22
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	6.084
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.482
MDCK Permeability:	0.00012055112892994657
Pgp-inhibitor:	0.995
Pgp-substrate:	0.363
Human Intestinal Absorption (HIA):	0.266
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	54.95957946777344%
Volume Distribution (VD):	0.149
Pgp-substrate:	13.279760360717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.61
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	0.812
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.243
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.3
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.915
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC307167

Natural Product ID:	NPC307167
*Common Name:**	Sid85149183
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:	(24S)-Pseudo-Ginsenoside F11
Standard InCHIKey:	JBGYSAVRIDZNKA-WBQAOMMUSA-N
Standard InCHI:	InChI=1S/C42H72O14/c1-19-28(46)30(48)32(50)35(52-19)55-33-31(49)29(47)23(18-43)54-36(33)53-22-17-41(8)24(39(6)13-11-25(45)37(2,3)34(22)39)16-21(44)27-20(10-14-40(27,41)7)42(9)15-12-26(56-42)38(4,5)51/h19-36,43-51H,10-18H2,1-9H3/t19-,20-,21+,22-,23+,24+,25-,26-,27-,28-,29+,30+,31-,32+,33+,34-,35-,36+,39+,40+,41+,42-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C[C@]3(C)[C@@H]([C@@]4([C@@H]2C(C)(C)[C@@H](O)CC4)C)C[C@H]([C@H]2[C@@]3(C)CC[C@@H]2[C@]2(C)CC[C@H](O2)C(O)(C)C)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509047
PubChem CID:	21637586
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
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350149]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28006911]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1
Potency	3

Activity Type	# Activity
Cell Line	1
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT136	Cell Line	SK-N-SH	Homo sapiens	Activity	=	103.0	%	PMID[527751]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1636.0	nM	PMID[527752]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	58.0	nM	PMID[527752]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	89125.1	nM	PMID[527752]

☑ 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 NPC307167 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	555
0.1-0.2	4996
0.2-0.3	13741
0.3-0.4	10607
0.4-0.5	5549
0.5-0.6	3650
0.6-0.7	1971
0.7-0.8	1099
0.8-0.85	265
0.85-0.9	99
0.9-0.95	108
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC210759
1.0	High Similarity	NPC229801
0.977	High Similarity	NPC45959
0.977	High Similarity	NPC305418
0.977	High Similarity	NPC252253
0.9765	High Similarity	NPC82955
0.9765	High Similarity	NPC131466
0.9655	High Similarity	NPC149400
0.9655	High Similarity	NPC88962
0.9655	High Similarity	NPC144790
0.9551	High Similarity	NPC237071
0.9551	High Similarity	NPC139271
0.9551	High Similarity	NPC476510
0.9551	High Similarity	NPC203434
0.9551	High Similarity	NPC238796
0.9551	High Similarity	NPC304011
0.9551	High Similarity	NPC142264
0.9545	High Similarity	NPC179859
0.9545	High Similarity	NPC174024
0.9545	High Similarity	NPC291547
0.9545	High Similarity	NPC131693
0.9545	High Similarity	NPC475436
0.9545	High Similarity	NPC312678
0.9545	High Similarity	NPC253268
0.9545	High Similarity	NPC24960
0.9545	High Similarity	NPC473851
0.9545	High Similarity	NPC473774
0.9529	High Similarity	NPC43912
0.9529	High Similarity	NPC140446
0.9444	High Similarity	NPC233649
0.9444	High Similarity	NPC470028
0.9444	High Similarity	NPC477222
0.9444	High Similarity	NPC477223
0.9438	High Similarity	NPC474399
0.9432	High Similarity	NPC48339
0.9432	High Similarity	NPC477547
0.9432	High Similarity	NPC250393
0.9432	High Similarity	NPC311246
0.9432	High Similarity	NPC177834
0.9432	High Similarity	NPC477451
0.9432	High Similarity	NPC249204
0.9432	High Similarity	NPC141769
0.9432	High Similarity	NPC325828
0.9432	High Similarity	NPC234352
0.9432	High Similarity	NPC297348
0.9432	High Similarity	NPC167644
0.9425	High Similarity	NPC65550
0.9425	High Similarity	NPC473542
0.9333	High Similarity	NPC121453
0.9326	High Similarity	NPC217205
0.9326	High Similarity	NPC309866
0.9326	High Similarity	NPC175
0.9326	High Similarity	NPC113500
0.9326	High Similarity	NPC291203
0.9326	High Similarity	NPC294686
0.9326	High Similarity	NPC471464
0.9326	High Similarity	NPC264101
0.9326	High Similarity	NPC477224
0.9326	High Similarity	NPC222731
0.9326	High Similarity	NPC3538
0.9318	High Similarity	NPC5632
0.9318	High Similarity	NPC204881
0.9318	High Similarity	NPC149966
0.9318	High Similarity	NPC473830
0.9294	High Similarity	NPC290612
0.9231	High Similarity	NPC274200
0.9231	High Similarity	NPC307534
0.9231	High Similarity	NPC475207
0.9231	High Similarity	NPC476112
0.9222	High Similarity	NPC57964
0.9222	High Similarity	NPC473064
0.9222	High Similarity	NPC107188
0.9222	High Similarity	NPC473727
0.9222	High Similarity	NPC211354
0.9222	High Similarity	NPC477494
0.9222	High Similarity	NPC107962
0.9222	High Similarity	NPC94582
0.9222	High Similarity	NPC473067
0.9222	High Similarity	NPC475351
0.9222	High Similarity	NPC92196
0.9222	High Similarity	NPC19400
0.9222	High Similarity	NPC206003
0.9222	High Similarity	NPC473610
0.9222	High Similarity	NPC6295
0.9222	High Similarity	NPC473065
0.9213	High Similarity	NPC172838
0.9213	High Similarity	NPC137004
0.9213	High Similarity	NPC473726
0.9205	High Similarity	NPC279329
0.9195	High Similarity	NPC281004
0.914	High Similarity	NPC472081
0.914	High Similarity	NPC108227
0.914	High Similarity	NPC475574
0.914	High Similarity	NPC476512
0.913	High Similarity	NPC473616
0.913	High Similarity	NPC473518
0.9121	High Similarity	NPC470865
0.9121	High Similarity	NPC470864
0.9121	High Similarity	NPC232037
0.9121	High Similarity	NPC184617
0.9121	High Similarity	NPC475625
0.9121	High Similarity	NPC98018
0.9121	High Similarity	NPC132080
0.9121	High Similarity	NPC97700
0.9121	High Similarity	NPC160426
0.9121	High Similarity	NPC473601
0.9121	High Similarity	NPC103616
0.9121	High Similarity	NPC128572
0.9121	High Similarity	NPC470863
0.9121	High Similarity	NPC30856
0.9121	High Similarity	NPC475643
0.9121	High Similarity	NPC84111
0.9121	High Similarity	NPC195297
0.9121	High Similarity	NPC284104
0.9121	High Similarity	NPC287483
0.9121	High Similarity	NPC116756
0.9121	High Similarity	NPC470866
0.9101	High Similarity	NPC293609
0.9101	High Similarity	NPC36372
0.9091	High Similarity	NPC20822
0.9091	High Similarity	NPC473472
0.9091	High Similarity	NPC102725
0.9043	High Similarity	NPC134967
0.9043	High Similarity	NPC114700
0.9043	High Similarity	NPC310138
0.9043	High Similarity	NPC470029
0.9022	High Similarity	NPC115165
0.9022	High Similarity	NPC303069
0.9022	High Similarity	NPC470861
0.9022	High Similarity	NPC51520
0.9022	High Similarity	NPC83137
0.9022	High Similarity	NPC232611
0.9022	High Similarity	NPC470862
0.9	High Similarity	NPC470623
0.9	High Similarity	NPC323231
0.9	High Similarity	NPC277774
0.9	High Similarity	NPC18724
0.9	High Similarity	NPC224003
0.9	High Similarity	NPC171741
0.8989	High Similarity	NPC223143
0.8947	High Similarity	NPC139181
0.8947	High Similarity	NPC476837
0.8947	High Similarity	NPC97260
0.8925	High Similarity	NPC291548
0.8925	High Similarity	NPC473638
0.8913	High Similarity	NPC296936
0.8901	High Similarity	NPC148593
0.8901	High Similarity	NPC473503
0.8901	High Similarity	NPC30687
0.8901	High Similarity	NPC191915
0.8901	High Similarity	NPC151214
0.8901	High Similarity	NPC267238
0.8901	High Similarity	NPC471373
0.8901	High Similarity	NPC77717
0.8901	High Similarity	NPC253611
0.8889	High Similarity	NPC473637
0.8889	High Similarity	NPC59006
0.8889	High Similarity	NPC476668
0.8817	High Similarity	NPC470591
0.8804	High Similarity	NPC469710
0.8804	High Similarity	NPC471424
0.8804	High Similarity	NPC189575
0.8804	High Similarity	NPC471429
0.8804	High Similarity	NPC205129
0.8804	High Similarity	NPC471425
0.8804	High Similarity	NPC106701
0.8791	High Similarity	NPC476669
0.8737	High Similarity	NPC477225
0.8737	High Similarity	NPC476838
0.8737	High Similarity	NPC476839
0.871	High Similarity	NPC252056
0.871	High Similarity	NPC472989
0.871	High Similarity	NPC473287
0.8696	High Similarity	NPC475325
0.8667	High Similarity	NPC228059
0.8652	High Similarity	NPC161928
0.8652	High Similarity	NPC472396
0.8652	High Similarity	NPC210658
0.8636	High Similarity	NPC232044
0.8636	High Similarity	NPC273290
0.8632	High Similarity	NPC470030
0.8621	High Similarity	NPC470070
0.8617	High Similarity	NPC210157
0.8586	High Similarity	NPC220427
0.8557	High Similarity	NPC120123
0.8557	High Similarity	NPC16520
0.8557	High Similarity	NPC472252
0.8557	High Similarity	NPC213190
0.8557	High Similarity	NPC189852
0.8557	High Similarity	NPC8039
0.8557	High Similarity	NPC114874
0.8557	High Similarity	NPC211879
0.8557	High Similarity	NPC131479
0.8557	High Similarity	NPC473020
0.8557	High Similarity	NPC286969
0.8557	High Similarity	NPC157659
0.8557	High Similarity	NPC155010
0.8557	High Similarity	NPC31907
0.8557	High Similarity	NPC245280
0.8556	High Similarity	NPC128475

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 NPC307167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	539
0.1-0.2	4586
0.2-0.3	2857
0.3-0.4	623
0.4-0.5	314
0.5-0.6	171
0.6-0.7	43
0.7-0.8	14
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9432	High Similarity	NPD8171	Discontinued
0.8469	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6928	Phase 2
0.7568	Intermediate Similarity	NPD8377	Approved
0.7568	Intermediate Similarity	NPD8294	Approved
0.7529	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.7386	Intermediate Similarity	NPD1810	Approved
0.7386	Intermediate Similarity	NPD1811	Approved
0.73	Intermediate Similarity	NPD7991	Discontinued
0.7232	Intermediate Similarity	NPD7327	Approved
0.7232	Intermediate Similarity	NPD7328	Approved
0.7168	Intermediate Similarity	NPD7516	Approved
0.7045	Intermediate Similarity	NPD2687	Approved
0.7045	Intermediate Similarity	NPD2254	Approved
0.7045	Intermediate Similarity	NPD2686	Approved
0.6972	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3669	Approved
0.6842	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD6940	Discontinued
0.6752	Remote Similarity	NPD7503	Approved
0.6727	Remote Similarity	NPD8174	Phase 2
0.6702	Remote Similarity	NPD6115	Approved
0.6702	Remote Similarity	NPD6118	Approved
0.6702	Remote Similarity	NPD6114	Approved
0.6702	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7319	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6596	Remote Similarity	NPD6116	Phase 1
0.6557	Remote Similarity	NPD7736	Approved
0.6552	Remote Similarity	NPD371	Approved
0.65	Remote Similarity	NPD8328	Phase 3
0.6489	Remote Similarity	NPD6117	Approved
0.6484	Remote Similarity	NPD4787	Phase 1
0.648	Remote Similarity	NPD8449	Approved
0.6429	Remote Similarity	NPD8450	Suspended
0.6417	Remote Similarity	NPD6370	Approved
0.6392	Remote Similarity	NPD7525	Registered
0.6341	Remote Similarity	NPD8293	Discontinued
0.6277	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6059	Approved
0.6237	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3703	Phase 2
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD1780	Approved
0.6162	Remote Similarity	NPD1779	Approved
0.614	Remote Similarity	NPD6686	Approved
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD7492	Approved
0.6023	Remote Similarity	NPD6123	Approved
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD6616	Approved
0.5985	Remote Similarity	NPD7625	Phase 1
0.5968	Remote Similarity	NPD6067	Discontinued
0.5962	Remote Similarity	NPD7524	Approved
0.596	Remote Similarity	NPD7645	Phase 2
0.5952	Remote Similarity	NPD7078	Approved
0.5935	Remote Similarity	NPD8513	Phase 3
0.5935	Remote Similarity	NPD8516	Approved
0.5935	Remote Similarity	NPD8515	Approved
0.5935	Remote Similarity	NPD8517	Approved
0.593	Remote Similarity	NPD2267	Suspended
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5360	Phase 3
0.5914	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD1700	Approved
0.5877	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3702	Approved
0.5865	Remote Similarity	NPD8308	Discontinued
0.5862	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7638	Approved
0.5825	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7640	Approved
0.5804	Remote Similarity	NPD7639	Approved
0.5798	Remote Similarity	NPD8297	Approved
0.5798	Remote Similarity	NPD6882	Approved
0.5794	Remote Similarity	NPD6700	Approved
0.5794	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4789	Approved
0.5789	Remote Similarity	NPD4245	Approved
0.5789	Remote Similarity	NPD4244	Approved
0.5781	Remote Similarity	NPD6033	Approved
0.5765	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD892	Phase 3
0.5765	Remote Similarity	NPD889	Approved
0.5765	Remote Similarity	NPD888	Phase 3
0.5765	Remote Similarity	NPD893	Approved
0.5765	Remote Similarity	NPD891	Phase 3
0.5765	Remote Similarity	NPD887	Approved
0.5765	Remote Similarity	NPD894	Approved
0.5765	Remote Similarity	NPD895	Approved
0.5741	Remote Similarity	NPD6702	Approved
0.5741	Remote Similarity	NPD6703	Approved
0.5738	Remote Similarity	NPD6009	Approved
0.5728	Remote Similarity	NPD6695	Phase 3
0.5726	Remote Similarity	NPD6319	Approved
0.5702	Remote Similarity	NPD7632	Discontinued
0.5684	Remote Similarity	NPD3698	Phase 2
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8418	Phase 2
0.566	Remote Similarity	NPD7750	Discontinued
0.5647	Remote Similarity	NPD2269	Approved
0.562	Remote Similarity	NPD4632	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