NPASS Compound

Structure

NPC470934 OpenBabel07101719522D 55 59 0 0 1 0 0 0 0 0999 V2000 6.1667 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4935 -7.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -8.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -6.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -8.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -6.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 -1.2459 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 5.3007 -5.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 -7.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 -8.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 -7.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -6.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4347 -7.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 -6.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 -4.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5686 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5686 -5.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6275 -8.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6308 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -5.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -7.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -8.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -7.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6275 -6.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 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 4.4347 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 47 1 0 0 0 0 3 48 1 0 0 0 0 4 7 2 0 0 0 0 4 18 1 0 0 0 0 5 8 2 0 0 0 0 5 19 1 0 0 0 0 6 9 2 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 49 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 50 1 0 0 0 0 15 36 1 0 0 0 0 15 37 1 0 0 0 0 16 36 1 0 0 0 0 16 51 1 0 0 0 0 17 1 1 6 0 0 0 17 26 1 0 0 0 0 17 52 1 0 0 0 0 20 22 2 0 0 0 0 20 38 1 0 0 0 0 21 23 2 0 0 0 0 21 39 1 0 0 0 0 22 47 1 0 0 0 0 23 48 1 0 0 0 0 24 14 1 1 0 0 0 24 30 1 0 0 0 0 24 53 1 0 0 0 0 25 40 2 0 0 0 0 25 54 1 0 0 0 0 26 27 1 0 0 0 0 26 41 1 1 0 0 0 27 28 1 0 0 0 0 27 42 1 6 0 0 0 28 34 1 0 0 0 0 28 43 1 6 0 0 0 29 31 1 0 0 0 0 29 33 1 0 0 0 0 29 44 1 6 0 0 0 30 31 1 0 0 0 0 30 54 1 6 0 0 0 31 55 1 1 0 0 0 32 35 1 0 0 0 0 32 36 1 1 0 0 0 32 45 1 0 0 0 0 33 49 1 1 0 0 0 33 53 1 0 0 0 0 34 52 1 0 0 0 0 34 55 1 1 0 0 0 35 50 1 6 0 0 0 35 51 1 0 0 0 0 36 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	784.28
Volume:	734.352
LogP:	0.664
LogD:	0.3
LogS:	-2.747
# Rotatable Bonds:	16
TPSA:	282.21
# H-Bond Aceptor:	19
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	5.331
Fsp3:	0.583
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.576
MDCK Permeability:	4.767491191159934e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.965
20% Bioavailability (F20%):	0.838
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	92.96700286865234%
Volume Distribution (VD):	0.161
Pgp-substrate:	8.531638145446777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	0.922
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.434
Human Hepatotoxicity (H-HT):	0.701
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.865
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC470934

Natural Product ID:	NPC470934
*Common Name:**	Lamiophlomiside
IUPAC Name:	[(2R,3R,4R,5R,6R)-2-[[(2S,3S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	Lamiophlomiside
Standard InCHIKey:	UMADJYFWGWTKSA-SMPKIETKSA-N
Standard InCHI:	InChI=1S/C36H48O19/c1-17-26(41)27(42)28(43)34(52-17)55-31-29(44)33(49-11-10-19-5-8-21(39)23(13-19)48-3)53-24(14-50-35-32(45)36(46,15-37)16-51-35)30(31)54-25(40)9-6-18-4-7-20(38)22(12-18)47-2/h4-9,12-13,17,24,26-35,37-39,41-46H,10-11,14-16H2,1-3H3/b9-6+/t17-,24-,26-,27+,28+,29-,30-,31-,32-,33-,34-,35+,36?/m1/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)COC4C(C(CO4)(CO)O)O)OCCC5=CC(=C(C=C5)O)OC)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL233095
PubChem CID:	44429864
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	12.73	%	PMID[556289]

☑ 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 NPC470934 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	327
0.1-0.2	1339
0.2-0.3	3145
0.3-0.4	7386
0.4-0.5	10050
0.5-0.6	7302
0.6-0.7	8380
0.7-0.8	4035
0.8-0.85	524
0.85-0.9	133
0.9-0.95	58
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188393
0.9653	High Similarity	NPC259347
0.9653	High Similarity	NPC476398
0.9653	High Similarity	NPC473427
0.9653	High Similarity	NPC94871
0.9653	High Similarity	NPC476386
0.9653	High Similarity	NPC471062
0.9653	High Similarity	NPC470933
0.9653	High Similarity	NPC306890
0.9648	High Similarity	NPC34927
0.9648	High Similarity	NPC100998
0.9648	High Similarity	NPC216819
0.9648	High Similarity	NPC34587
0.9648	High Similarity	NPC252292
0.9648	High Similarity	NPC476382
0.9648	High Similarity	NPC83743
0.9648	High Similarity	NPC287615
0.9648	High Similarity	NPC262182
0.9586	High Similarity	NPC257970
0.9586	High Similarity	NPC470927
0.9583	High Similarity	NPC201148
0.9583	High Similarity	NPC199311
0.9583	High Similarity	NPC210611
0.9583	High Similarity	NPC28651
0.9583	High Similarity	NPC300262
0.9583	High Similarity	NPC3460
0.9583	High Similarity	NPC192763
0.9583	High Similarity	NPC215095
0.9583	High Similarity	NPC80732
0.9583	High Similarity	NPC261122
0.9577	High Similarity	NPC300894
0.9577	High Similarity	NPC141455
0.9577	High Similarity	NPC196063
0.9577	High Similarity	NPC110063
0.9577	High Similarity	NPC296954
0.9514	High Similarity	NPC232992
0.9507	High Similarity	NPC105005
0.9456	High Similarity	NPC478268
0.9444	High Similarity	NPC229505
0.9444	High Similarity	NPC476865
0.9437	High Similarity	NPC140502
0.9388	High Similarity	NPC7145
0.9388	High Similarity	NPC85192
0.9388	High Similarity	NPC143480
0.9388	High Similarity	NPC125823
0.9384	High Similarity	NPC283839
0.9384	High Similarity	NPC90896
0.9375	High Similarity	NPC476864
0.9375	High Similarity	NPC476868
0.9375	High Similarity	NPC476866
0.9375	High Similarity	NPC476869
0.9366	High Similarity	NPC47471
0.9366	High Similarity	NPC476377
0.9366	High Similarity	NPC476385
0.9366	High Similarity	NPC134405
0.9324	High Similarity	NPC289967
0.9324	High Similarity	NPC472612
0.9324	High Similarity	NPC472611
0.9306	High Similarity	NPC476867
0.9296	High Similarity	NPC473799
0.9296	High Similarity	NPC475530
0.9236	High Similarity	NPC269141
0.9236	High Similarity	NPC476397
0.9236	High Similarity	NPC298257
0.9236	High Similarity	NPC476378
0.9236	High Similarity	NPC476380
0.9236	High Similarity	NPC205864
0.9236	High Similarity	NPC478239
0.9236	High Similarity	NPC175214
0.9236	High Similarity	NPC112
0.9236	High Similarity	NPC76406
0.9236	High Similarity	NPC119537
0.9236	High Similarity	NPC476375
0.9236	High Similarity	NPC40305
0.9236	High Similarity	NPC96795
0.9236	High Similarity	NPC476384
0.9236	High Similarity	NPC264632
0.9236	High Similarity	NPC247032
0.9236	High Similarity	NPC476381
0.9225	High Similarity	NPC321184
0.9225	High Similarity	NPC472350
0.9225	High Similarity	NPC328273
0.9225	High Similarity	NPC64141
0.9225	High Similarity	NPC205195
0.9225	High Similarity	NPC321638
0.9225	High Similarity	NPC89105
0.9225	High Similarity	NPC197316
0.9225	High Similarity	NPC476383
0.9225	High Similarity	NPC81515
0.9225	High Similarity	NPC171134
0.9225	High Similarity	NPC68092
0.9225	High Similarity	NPC226005
0.9205	High Similarity	NPC11411
0.9189	High Similarity	NPC476871
0.9172	High Similarity	NPC64195
0.9167	High Similarity	NPC157816
0.9167	High Similarity	NPC222433
0.9167	High Similarity	NPC265648
0.9155	High Similarity	NPC78363
0.9155	High Similarity	NPC260425
0.9122	High Similarity	NPC106138
0.9122	High Similarity	NPC478242
0.9103	High Similarity	NPC113680
0.9103	High Similarity	NPC278961
0.9097	High Similarity	NPC186406
0.9091	High Similarity	NPC7191
0.9091	High Similarity	NPC149873
0.9085	High Similarity	NPC478269
0.9085	High Similarity	NPC157554
0.906	High Similarity	NPC475224
0.9048	High Similarity	NPC199928
0.9041	High Similarity	NPC297342
0.9041	High Similarity	NPC232228
0.9034	High Similarity	NPC473792
0.9034	High Similarity	NPC473873
0.9032	High Similarity	NPC246024
0.9028	High Similarity	NPC202700
0.9026	High Similarity	NPC478265
0.9021	High Similarity	NPC476376
0.902	High Similarity	NPC226759
0.8973	High Similarity	NPC46092
0.8968	High Similarity	NPC478267
0.8966	High Similarity	NPC472711
0.8958	High Similarity	NPC100389
0.8954	High Similarity	NPC478266
0.8951	High Similarity	NPC52277
0.8951	High Similarity	NPC199459
0.8951	High Similarity	NPC177035
0.8944	High Similarity	NPC470881
0.8944	High Similarity	NPC471883
0.8944	High Similarity	NPC135127
0.8944	High Similarity	NPC287597
0.8944	High Similarity	NPC34293
0.8944	High Similarity	NPC886
0.8944	High Similarity	NPC35731
0.8912	High Similarity	NPC84181
0.8912	High Similarity	NPC470235
0.8912	High Similarity	NPC471063
0.8912	High Similarity	NPC283995
0.8912	High Similarity	NPC292443
0.8912	High Similarity	NPC129417
0.8897	High Similarity	NPC106944
0.8889	High Similarity	NPC304152
0.8889	High Similarity	NPC126206
0.8889	High Similarity	NPC138738
0.8889	High Similarity	NPC131532
0.8889	High Similarity	NPC470413
0.8881	High Similarity	NPC476870
0.8874	High Similarity	NPC269914
0.8874	High Similarity	NPC478249
0.8873	High Similarity	NPC254398
0.8873	High Similarity	NPC6836
0.8861	High Similarity	NPC59516
0.8851	High Similarity	NPC473909
0.8851	High Similarity	NPC143120
0.8851	High Similarity	NPC274960
0.8851	High Similarity	NPC18979
0.8844	High Similarity	NPC470950
0.8844	High Similarity	NPC185307
0.8844	High Similarity	NPC477898
0.8831	High Similarity	NPC478248
0.8831	High Similarity	NPC228357
0.8819	High Similarity	NPC471665
0.8819	High Similarity	NPC471664
0.8819	High Similarity	NPC37468
0.8819	High Similarity	NPC186418
0.8816	High Similarity	NPC106818
0.8805	High Similarity	NPC208818
0.8803	High Similarity	NPC473924
0.8803	High Similarity	NPC252833
0.8803	High Similarity	NPC473285
0.88	High Similarity	NPC478237
0.8792	High Similarity	NPC112861
0.8792	High Similarity	NPC276753
0.8792	High Similarity	NPC205796
0.8776	High Similarity	NPC476356
0.8776	High Similarity	NPC67467
0.8774	High Similarity	NPC471878
0.8766	High Similarity	NPC38699
0.8758	High Similarity	NPC245615
0.8758	High Similarity	NPC150442
0.8758	High Similarity	NPC299706
0.8758	High Similarity	NPC87403
0.8758	High Similarity	NPC115466
0.8758	High Similarity	NPC44730
0.8758	High Similarity	NPC61604
0.875	High Similarity	NPC263829
0.8732	High Similarity	NPC46137
0.8732	High Similarity	NPC248307
0.8732	High Similarity	NPC246869
0.8732	High Similarity	NPC235294
0.8732	High Similarity	NPC219677
0.8732	High Similarity	NPC138777
0.8732	High Similarity	NPC225384
0.8732	High Similarity	NPC65942
0.8732	High Similarity	NPC478255
0.8725	High Similarity	NPC38041
0.8725	High Similarity	NPC279298
0.8725	High Similarity	NPC22150
0.871	High Similarity	NPC163635

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 NPC470934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	776
0.2-0.3	1678
0.3-0.4	2795
0.4-0.5	2051
0.5-0.6	1087
0.6-0.7	443
0.7-0.8	52
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD7266	Discontinued
0.8377	Intermediate Similarity	NPD1653	Approved
0.8364	Intermediate Similarity	NPD7685	Pre-registration
0.8232	Intermediate Similarity	NPD7228	Approved
0.8133	Intermediate Similarity	NPD7472	Approved
0.8072	Intermediate Similarity	NPD7054	Approved
0.8059	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7959	Intermediate Similarity	NPD3027	Phase 3
0.7929	Intermediate Similarity	NPD7251	Discontinued
0.7914	Intermediate Similarity	NPD6234	Discontinued
0.7904	Intermediate Similarity	NPD3818	Discontinued
0.787	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD37	Approved
0.7824	Intermediate Similarity	NPD7240	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8455	Phase 2
0.7756	Intermediate Similarity	NPD6190	Approved
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1613	Approved
0.7671	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3705	Approved
0.7628	Intermediate Similarity	NPD6674	Discontinued
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1357	Approved
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1091	Approved
0.7405	Intermediate Similarity	NPD7680	Approved
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7394	Intermediate Similarity	NPD1934	Approved
0.7377	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5058	Phase 3
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2977	Approved
0.7349	Intermediate Similarity	NPD2978	Approved
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7097	Phase 1
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7254	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7246	Intermediate Similarity	NPD1465	Phase 2
0.7246	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5844	Phase 1
0.7202	Intermediate Similarity	NPD3817	Phase 2
0.7192	Intermediate Similarity	NPD5536	Phase 2
0.7169	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.7118	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD230	Phase 1
0.707	Intermediate Similarity	NPD4340	Discontinued
0.707	Intermediate Similarity	NPD5124	Phase 1
0.7066	Intermediate Similarity	NPD7028	Phase 2
0.7051	Intermediate Similarity	NPD6233	Phase 2
0.7035	Intermediate Similarity	NPD5494	Approved
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7025	Intermediate Similarity	NPD6653	Approved
0.7018	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5402	Approved
0.6989	Remote Similarity	NPD3751	Discontinued
0.6983	Remote Similarity	NPD7549	Discontinued
0.6975	Remote Similarity	NPD4237	Approved
0.6975	Remote Similarity	NPD4236	Phase 3
0.6974	Remote Similarity	NPD2983	Phase 2
0.6974	Remote Similarity	NPD2982	Phase 2
0.6972	Remote Similarity	NPD1358	Approved
0.6968	Remote Similarity	NPD4908	Phase 1
0.6966	Remote Similarity	NPD7843	Approved
0.6962	Remote Similarity	NPD6355	Discontinued
0.6962	Remote Similarity	NPD1933	Approved
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6954	Remote Similarity	NPD6232	Discontinued
0.6946	Remote Similarity	NPD3687	Approved
0.6946	Remote Similarity	NPD3686	Approved
0.6943	Remote Similarity	NPD8151	Discontinued
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5588	Approved
0.6937	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD5125	Phase 3
0.6933	Remote Similarity	NPD5126	Approved
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4110	Phase 3
0.6932	Remote Similarity	NPD7473	Discontinued
0.6928	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD6385	Approved
0.6909	Remote Similarity	NPD4357	Discontinued
0.6909	Remote Similarity	NPD1511	Approved
0.6908	Remote Similarity	NPD2981	Phase 2
0.6905	Remote Similarity	NPD7458	Discontinued
0.6903	Remote Similarity	NPD9494	Approved
0.6903	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD1558	Phase 1
0.6894	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD3496	Discontinued
0.6886	Remote Similarity	NPD5403	Approved
0.6885	Remote Similarity	NPD6842	Approved
0.6885	Remote Similarity	NPD6841	Approved
0.6885	Remote Similarity	NPD6843	Phase 3
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4538	Approved
0.6875	Remote Similarity	NPD4536	Approved
0.6875	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3060	Approved
0.6871	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7435	Discontinued
0.6857	Remote Similarity	NPD3787	Discontinued
0.6852	Remote Similarity	NPD1375	Discontinued
0.6848	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD422	Phase 1
0.6833	Remote Similarity	NPD7038	Approved
0.6833	Remote Similarity	NPD7039	Approved
0.6829	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1512	Approved
0.6824	Remote Similarity	NPD7157	Approved
0.6813	Remote Similarity	NPD2492	Phase 1
0.681	Remote Similarity	NPD2424	Discontinued
0.6805	Remote Similarity	NPD3455	Phase 2
0.6793	Remote Similarity	NPD7906	Approved
0.6792	Remote Similarity	NPD4140	Approved
0.6788	Remote Similarity	NPD7999	Approved
0.6786	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7783	Phase 2
0.6784	Remote Similarity	NPD6801	Discontinued
0.6783	Remote Similarity	NPD3134	Approved
0.6781	Remote Similarity	NPD969	Suspended
0.6771	Remote Similarity	NPD7698	Approved
0.6771	Remote Similarity	NPD7696	Phase 3
0.6771	Remote Similarity	NPD7697	Approved
0.6768	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5401	Approved
0.6763	Remote Similarity	NPD7768	Phase 2
0.6759	Remote Similarity	NPD3022	Approved
0.6759	Remote Similarity	NPD3021	Approved
0.675	Remote Similarity	NPD447	Suspended
0.6748	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5772	Approved
0.6744	Remote Similarity	NPD5773	Approved
0.6744	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7874	Approved
0.6735	Remote Similarity	NPD5535	Approved
0.6735	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1610	Phase 2
0.673	Remote Similarity	NPD4062	Phase 3
0.6728	Remote Similarity	NPD4108	Discontinued
0.6728	Remote Similarity	NPD5960	Phase 3
0.6727	Remote Similarity	NPD3750	Approved
0.6727	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6273	Approved
0.6725	Remote Similarity	NPD7411	Suspended
0.6719	Remote Similarity	NPD6823	Phase 2
0.6718	Remote Similarity	NPD7701	Phase 2
0.6711	Remote Similarity	NPD4626	Approved
0.6711	Remote Similarity	NPD6671	Approved
0.671	Remote Similarity	NPD3225	Approved
0.671	Remote Similarity	NPD8651	Approved
0.6707	Remote Similarity	NPD6799	Approved
0.6705	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5353	Approved
0.6705	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6781	Approved
0.6702	Remote Similarity	NPD6780	Approved
0.6702	Remote Similarity	NPD6778	Approved
0.6702	Remote Similarity	NPD6782	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