NPASS Compound

Structure

NPC309866 OpenBabel07101718332D 54 59 0 0 1 0 0 0 0 0999 V2000 -4.2216 -1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5088 -2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1413 -6.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2637 -3.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9439 -4.8519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 -5.1711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1705 -4.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9958 -2.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3977 -4.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -3.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 -3.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5317 -4.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8618 -4.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 -6.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5306 -2.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 -6.1222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8615 -3.4769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8618 -3.1609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9958 -4.6609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9958 -5.6609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2637 -4.6609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7885 -6.3301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1953 -7.2436 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1898 -7.1391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3977 -6.1609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9344 -0.6237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1298 -4.1609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5317 -5.6609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2637 -5.6609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7278 -2.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8618 -6.1609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 -2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6953 -8.1096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8589 -7.8822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2637 -6.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -2.6453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -1.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6036 0.1194 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 -1.2872 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 6 50 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 27 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 51 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 16 40 1 0 0 0 0 17 26 1 0 0 0 0 17 52 1 0 0 0 0 18 25 1 0 0 0 0 18 53 1 0 0 0 0 19 21 1 0 0 0 0 20 3 1 1 0 0 0 20 28 1 0 0 0 0 21 8 1 1 0 0 0 22 41 1 1 0 0 0 23 24 1 0 0 0 0 23 38 1 1 0 0 0 24 42 1 6 0 0 0 25 29 1 0 0 0 0 25 43 1 1 0 0 0 26 30 1 0 0 0 0 26 44 1 1 0 0 0 27 38 1 1 0 0 0 27 40 1 0 0 0 0 28 31 1 0 0 0 0 28 39 1 1 0 0 0 29 33 1 0 0 0 0 29 45 1 6 0 0 0 30 34 1 0 0 0 0 30 46 1 6 0 0 0 31 32 1 0 0 0 0 31 47 1 1 0 0 0 32 35 1 0 0 0 0 32 48 1 1 0 0 0 33 37 1 0 0 0 0 33 50 1 1 0 0 0 34 36 1 0 0 0 0 34 54 1 1 0 0 0 35 39 1 1 0 0 0 35 40 1 0 0 0 0 36 51 1 6 0 0 0 36 52 1 0 0 0 0 37 53 1 0 0 0 0 37 54 1 6 0 0 0 38 4 1 1 0 0 0 39 5 1 1 0 0 0 40 49 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	774.48
Volume:	772.12
LogP:	2.702
LogD:	3.01
LogS:	-3.146
# Rotatable Bonds:	12
TPSA:	228.22
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	6.103
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:	-5.807
MDCK Permeability:	9.410532948095351e-05
Pgp-inhibitor:	0.305
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.8
20% Bioavailability (F20%):	0.192
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	73.22469329833984%
Volume Distribution (VD):	0.096
Pgp-substrate:	8.943392753601074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.392
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	0.755
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.566
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.925
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC309866

Natural Product ID:	NPC309866
*Common Name:**	Halityloside B
IUPAC Name:	(3S,5S,6S,8S,9R,10S,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-[2-[(2R,3R,4S,5R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyethyl]-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15,16-pentol
Synonyms:
Standard InCHIKey:	LUQPNFAPDCHUPR-NGFLEQHHSA-N
Standard InCHI:	InChI=1S/C40H70O14/c1-19(2)21(11-14-51-36-34(30(46)26(44)17-52-36)54-37-33(50-6)29(45)25(43)18-53-37)8-7-20(3)28-31(47)32(48)35-39(28,5)13-10-27-38(4)12-9-22(41)15-23(38)24(42)16-40(27,35)49/h19-37,41-49H,7-18H2,1-6H3/t20-,21-,22+,23-,24+,25-,26-,27-,28+,29+,30+,31-,32-,33-,34-,35-,36-,37+,38+,39-,40+/m1/s1
SMILES:	CO[C@H]1[C@@H](OC[C@H]([C@@H]1O)O)O[C@H]1[C@H](OCC[C@H](C(C)C)CC[C@H]([C@H]2[C@@H](O)[C@H]([C@@H]3[C@]2(C)CC[C@H]2[C@@]3(O)C[C@@H]([C@@H]3[C@]2(C)CC[C@@H](C3)O)O)O)C)OC[C@H]([C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507915
PubChem CID:	13990011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO33455	nardoa tuberculata	Species	Ophidiasteridae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[8377014]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6256	Organism	Sphaerechinus granularis	Sphaerechinus granularis	LD50	=	1.0	10'-5M	PMID[481413]

☑ 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 NPC309866 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	583
0.1-0.2	5194
0.2-0.3	13258
0.3-0.4	10938
0.4-0.5	5483
0.5-0.6	3576
0.6-0.7	2028
0.7-0.8	1163
0.8-0.85	228
0.85-0.9	73
0.9-0.95	161
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC92196
0.977	High Similarity	NPC204881
0.977	High Similarity	NPC473830
0.977	High Similarity	NPC36372
0.9659	High Similarity	NPC277774
0.9655	High Similarity	NPC279329
0.9655	High Similarity	NPC65550
0.9551	High Similarity	NPC45959
0.9551	High Similarity	NPC252253
0.9551	High Similarity	NPC473774
0.9551	High Similarity	NPC24960
0.9545	High Similarity	NPC293609
0.954	High Similarity	NPC102725
0.954	High Similarity	NPC131466
0.9451	High Similarity	NPC470028
0.9451	High Similarity	NPC233649
0.9451	High Similarity	NPC477223
0.9451	High Similarity	NPC477222
0.9444	High Similarity	NPC474399
0.9438	High Similarity	NPC144790
0.9438	High Similarity	NPC137004
0.9438	High Similarity	NPC172838
0.9438	High Similarity	NPC311246
0.9438	High Similarity	NPC88962
0.9438	High Similarity	NPC149400
0.9438	High Similarity	NPC473726
0.9438	High Similarity	NPC167644
0.9432	High Similarity	NPC223143
0.9425	High Similarity	NPC281004
0.9341	High Similarity	NPC473287
0.9341	High Similarity	NPC142264
0.9341	High Similarity	NPC296936
0.9341	High Similarity	NPC139271
0.9341	High Similarity	NPC304011
0.9341	High Similarity	NPC476510
0.9333	High Similarity	NPC3538
0.9333	High Similarity	NPC253268
0.9333	High Similarity	NPC312678
0.9333	High Similarity	NPC113500
0.9333	High Similarity	NPC131693
0.9333	High Similarity	NPC291547
0.9333	High Similarity	NPC475436
0.9333	High Similarity	NPC473851
0.9333	High Similarity	NPC473503
0.9333	High Similarity	NPC477224
0.9333	High Similarity	NPC179859
0.9333	High Similarity	NPC174024
0.9326	High Similarity	NPC307167
0.9326	High Similarity	NPC210759
0.9326	High Similarity	NPC229801
0.9318	High Similarity	NPC473472
0.931	High Similarity	NPC43912
0.931	High Similarity	NPC140446
0.9239	High Similarity	NPC274200
0.9231	High Similarity	NPC469710
0.9231	High Similarity	NPC477494
0.9231	High Similarity	NPC473067
0.9231	High Similarity	NPC473064
0.9231	High Similarity	NPC473065
0.9222	High Similarity	NPC297348
0.9222	High Similarity	NPC477451
0.9222	High Similarity	NPC477547
0.9222	High Similarity	NPC177834
0.9222	High Similarity	NPC234352
0.9222	High Similarity	NPC250393
0.9222	High Similarity	NPC141769
0.9222	High Similarity	NPC325828
0.9222	High Similarity	NPC48339
0.9222	High Similarity	NPC249204
0.9213	High Similarity	NPC473542
0.9149	High Similarity	NPC475574
0.9149	High Similarity	NPC476839
0.9149	High Similarity	NPC476838
0.914	High Similarity	NPC473616
0.913	High Similarity	NPC121453
0.9121	High Similarity	NPC475325
0.9121	High Similarity	NPC217205
0.9121	High Similarity	NPC471464
0.9121	High Similarity	NPC222731
0.9121	High Similarity	NPC305418
0.9121	High Similarity	NPC264101
0.9121	High Similarity	NPC175
0.9121	High Similarity	NPC291203
0.9121	High Similarity	NPC294686
0.9111	High Similarity	NPC149966
0.9111	High Similarity	NPC473637
0.9111	High Similarity	NPC5632
0.9111	High Similarity	NPC476668
0.9101	High Similarity	NPC82955
0.908	High Similarity	NPC290612
0.9053	High Similarity	NPC134967
0.9053	High Similarity	NPC114700
0.9053	High Similarity	NPC310138
0.9053	High Similarity	NPC470029
0.9032	High Similarity	NPC470591
0.9032	High Similarity	NPC476112
0.9032	High Similarity	NPC475207
0.9032	High Similarity	NPC210157
0.9032	High Similarity	NPC307534
0.9022	High Similarity	NPC473610
0.9022	High Similarity	NPC211354
0.9022	High Similarity	NPC6295
0.9022	High Similarity	NPC107962
0.9022	High Similarity	NPC19400
0.9022	High Similarity	NPC473727
0.9022	High Similarity	NPC206003
0.9022	High Similarity	NPC475351
0.9022	High Similarity	NPC57964
0.9022	High Similarity	NPC94582
0.9022	High Similarity	NPC107188
0.9011	High Similarity	NPC476669
0.8947	High Similarity	NPC476512
0.8947	High Similarity	NPC472081
0.8947	High Similarity	NPC108227
0.8936	High Similarity	NPC291548
0.8936	High Similarity	NPC473518
0.8936	High Similarity	NPC473638
0.8925	High Similarity	NPC30856
0.8925	High Similarity	NPC287483
0.8925	High Similarity	NPC128572
0.8925	High Similarity	NPC103616
0.8925	High Similarity	NPC184617
0.8925	High Similarity	NPC84111
0.8925	High Similarity	NPC195297
0.8925	High Similarity	NPC203434
0.8925	High Similarity	NPC475643
0.8925	High Similarity	NPC116756
0.8925	High Similarity	NPC284104
0.8925	High Similarity	NPC470866
0.8925	High Similarity	NPC98018
0.8925	High Similarity	NPC97700
0.8925	High Similarity	NPC470863
0.8925	High Similarity	NPC232037
0.8925	High Similarity	NPC470865
0.8925	High Similarity	NPC475625
0.8925	High Similarity	NPC160426
0.8925	High Similarity	NPC473601
0.8925	High Similarity	NPC470864
0.8925	High Similarity	NPC132080
0.8925	High Similarity	NPC237071
0.8925	High Similarity	NPC238796
0.8901	High Similarity	NPC59006
0.8889	High Similarity	NPC20822
0.8876	High Similarity	NPC472396
0.8866	High Similarity	NPC475521
0.883	High Similarity	NPC303069
0.883	High Similarity	NPC470862
0.883	High Similarity	NPC51520
0.883	High Similarity	NPC83137
0.883	High Similarity	NPC115165
0.883	High Similarity	NPC470861
0.883	High Similarity	NPC232611
0.8763	High Similarity	NPC139181
0.8763	High Similarity	NPC476837
0.8763	High Similarity	NPC97260
0.875	High Similarity	NPC477172
0.875	High Similarity	NPC477225
0.871	High Similarity	NPC191915
0.871	High Similarity	NPC30687
0.871	High Similarity	NPC151214
0.8681	High Similarity	NPC228059
0.8646	High Similarity	NPC20028
0.8602	High Similarity	NPC224003
0.8602	High Similarity	NPC470623
0.8602	High Similarity	NPC18724
0.8602	High Similarity	NPC323231
0.8602	High Similarity	NPC171741
0.86	High Similarity	NPC475634
0.8556	High Similarity	NPC471240
0.8539	High Similarity	NPC474156
0.8526	High Similarity	NPC156377
0.8526	High Similarity	NPC472989
0.8526	High Similarity	NPC252056
0.8515	High Similarity	NPC474573
0.8511	High Similarity	NPC471373
0.8511	High Similarity	NPC77717
0.8511	High Similarity	NPC253611
0.8511	High Similarity	NPC148593
0.8511	High Similarity	NPC267238
0.85	High Similarity	NPC473469
0.8469	Intermediate Similarity	NPC310031
0.8469	Intermediate Similarity	NPC80191
0.8462	Intermediate Similarity	NPC161928
0.8462	Intermediate Similarity	NPC210658
0.8454	Intermediate Similarity	NPC470030
0.8454	Intermediate Similarity	NPC41843
0.8444	Intermediate Similarity	NPC232044
0.8444	Intermediate Similarity	NPC273290
0.8438	Intermediate Similarity	NPC76486
0.8427	Intermediate Similarity	NPC241959
0.8421	Intermediate Similarity	NPC106701
0.8421	Intermediate Similarity	NPC205129
0.8421	Intermediate Similarity	NPC471425
0.8421	Intermediate Similarity	NPC471424
0.8421	Intermediate Similarity	NPC471429
0.8421	Intermediate Similarity	NPC189575
0.8384	Intermediate Similarity	NPC120123
0.8384	Intermediate Similarity	NPC189852
0.8384	Intermediate Similarity	NPC245280
0.8384	Intermediate Similarity	NPC8039

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 NPC309866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	578
0.1-0.2	4658
0.2-0.3	2743
0.3-0.4	610
0.4-0.5	300
0.5-0.6	204
0.6-0.7	40
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9222	High Similarity	NPD8171	Discontinued
0.83	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6928	Phase 2
0.7679	Intermediate Similarity	NPD8379	Approved
0.7679	Intermediate Similarity	NPD8296	Approved
0.7679	Intermediate Similarity	NPD8335	Approved
0.7679	Intermediate Similarity	NPD8380	Approved
0.7679	Intermediate Similarity	NPD8378	Approved
0.7589	Intermediate Similarity	NPD8377	Approved
0.7589	Intermediate Similarity	NPD8294	Approved
0.7523	Intermediate Similarity	NPD8133	Approved
0.7522	Intermediate Similarity	NPD8033	Approved
0.7411	Intermediate Similarity	NPD7327	Approved
0.7411	Intermediate Similarity	NPD7328	Approved
0.7356	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7516	Approved
0.7222	Intermediate Similarity	NPD1810	Approved
0.7222	Intermediate Similarity	NPD1811	Approved
0.7157	Intermediate Similarity	NPD7991	Discontinued
0.6923	Remote Similarity	NPD7503	Approved
0.6889	Remote Similarity	NPD2686	Approved
0.6889	Remote Similarity	NPD2687	Approved
0.6889	Remote Similarity	NPD2254	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7507	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD7319	Approved
0.6735	Remote Similarity	NPD3669	Approved
0.6735	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4787	Phase 1
0.6638	Remote Similarity	NPD6940	Discontinued
0.6607	Remote Similarity	NPD8174	Phase 2
0.6591	Remote Similarity	NPD371	Approved
0.6585	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD6118	Approved
0.6562	Remote Similarity	NPD6115	Approved
0.6562	Remote Similarity	NPD6697	Approved
0.6562	Remote Similarity	NPD6114	Approved
0.6458	Remote Similarity	NPD6116	Phase 1
0.6446	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD8328	Phase 3
0.6378	Remote Similarity	NPD8449	Approved
0.6371	Remote Similarity	NPD8293	Discontinued
0.6354	Remote Similarity	NPD6117	Approved
0.6328	Remote Similarity	NPD8450	Suspended
0.6281	Remote Similarity	NPD6054	Approved
0.6281	Remote Similarity	NPD6059	Approved
0.6263	Remote Similarity	NPD7525	Registered
0.6146	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6016	Approved
0.6098	Remote Similarity	NPD6015	Approved
0.6082	Remote Similarity	NPD3702	Approved
0.6082	Remote Similarity	NPD3703	Phase 2
0.608	Remote Similarity	NPD7492	Approved
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD8035	Phase 2
0.6048	Remote Similarity	NPD5988	Approved
0.604	Remote Similarity	NPD1780	Approved
0.604	Remote Similarity	NPD1779	Approved
0.6034	Remote Similarity	NPD6686	Approved
0.6032	Remote Similarity	NPD6616	Approved
0.6016	Remote Similarity	NPD6319	Approved
0.6014	Remote Similarity	NPD7625	Phase 1
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD4245	Approved
0.5984	Remote Similarity	NPD7078	Approved
0.5966	Remote Similarity	NPD6882	Approved
0.5966	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD1700	Approved
0.5913	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6009	Approved
0.5897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3698	Phase 2
0.5895	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7638	Approved
0.5889	Remote Similarity	NPD6123	Approved
0.5865	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7645	Phase 2
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.5814	Remote Similarity	NPD6033	Approved
0.581	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5360	Phase 3
0.5789	Remote Similarity	NPD4159	Approved
0.5789	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4632	Approved
0.5773	Remote Similarity	NPD5777	Approved
0.5769	Remote Similarity	NPD6695	Phase 3
0.5755	Remote Similarity	NPD8308	Discontinued
0.5739	Remote Similarity	NPD7632	Discontinued
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8516	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD8513	Phase 3
0.5714	Remote Similarity	NPD8515	Approved
0.5714	Remote Similarity	NPD8517	Approved
0.5701	Remote Similarity	NPD7750	Discontinued
0.5688	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6700	Approved
0.5678	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.567	Remote Similarity	NPD4789	Approved
0.5667	Remote Similarity	NPD4634	Approved
0.5636	Remote Similarity	NPD6703	Approved
0.5636	Remote Similarity	NPD6702	Approved
0.5632	Remote Similarity	NPD892	Phase 3
0.5632	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD888	Phase 3
0.5632	Remote Similarity	NPD893	Approved
0.5632	Remote Similarity	NPD891	Phase 3
0.5631	Remote Similarity	NPD4748	Discontinued
0.563	Remote Similarity	NPD6899	Approved
0.563	Remote Similarity	NPD7320	Approved
0.563	Remote Similarity	NPD6881	Approved
0.562	Remote Similarity	NPD6650	Approved
0.562	Remote Similarity	NPD6649	Approved
0.562	Remote Similarity	NPD8130	Phase 1

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