NPASS Compound

Structure

NPC474345 OpenBabel07101718312D 38 41 0 0 1 0 0 0 0 0999 V2000 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 19 2 0 0 0 0 11 20 1 0 0 0 0 11 28 2 0 0 0 0 12 3 1 6 0 0 0 12 23 1 0 0 0 0 12 35 1 0 0 0 0 13 29 2 0 0 0 0 13 36 1 0 0 0 0 14 30 2 0 0 0 0 14 37 1 0 0 0 0 15 38 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 21 1 0 0 0 0 18 31 1 0 0 0 0 19 22 1 0 0 0 0 19 32 1 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 6 0 0 0 24 34 2 0 0 0 0 25 26 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 35 1 0 0 0 0 27 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.16
Volume:	511.65
LogP:	3.762
LogD:	1.931
LogS:	-4.472
# Rotatable Bonds:	7
TPSA:	169.05
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	4.322
Fsp3:	0.37
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.748
MDCK Permeability:	4.2476483940845355e-05
Pgp-inhibitor:	0.548
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.698
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	90.36003875732422%
Volume Distribution (VD):	0.949
Pgp-substrate:	10.611763954162598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.762
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.407
CYP2D6-inhibitor:	0.815
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	0.993
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.608
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.382
Skin Sensitization:	0.818
Carcinogencity:	0.136
Eye Corrosion:	0.006
Eye Irritation:	0.177
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC474345

Natural Product ID:	NPC474345
*Common Name:**	[(2S,3R,4S,5R,6S)-2-[(9-Acetyl-4,5-Dihydroxy-7-Methyl-10-Oxo-9H-Anthracen-2-Yl)Oxy]-3-Acetyloxy-5-Hydroxy-6-Methyloxan-4-Yl] Acetate
IUPAC Name:	[(2S,3R,4S,5R,6S)-2-[(9-acetyl-4,5-dihydroxy-7-methyl-10-oxo-9H-anthracen-2-yl)oxy]-3-acetyloxy-5-hydroxy-6-methyloxan-4-yl] acetate
Synonyms:
Standard InCHIKey:	YCSCGCFLJRBNIA-NZFLMTEZSA-N
Standard InCHI:	InChI=1S/C27H28O11/c1-10-6-16-20(11(2)28)17-8-15(9-19(32)22(17)24(34)21(16)18(31)7-10)38-27-26(37-14(5)30)25(36-13(4)29)23(33)12(3)35-27/h6-9,12,20,23,25-27,31-33H,1-5H3/t12-,20?,23+,25-,26+,27-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](Oc2cc(O)c3c(c2)C(C(=O)C)c2c(C3=O)c(O)cc(c2)C)O[C@H]([C@H]([C@@H]1OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465493
PubChem CID:	44567191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO32935	rhamnus nepalensis	Species	Rhamnaceae	Eukaryota	Leaves	Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam	1995-Nov	PMID[11575949]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	70.0	nM	PMID[477099]

☑ 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 NPC474345 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	386
0.1-0.2	1592
0.2-0.3	3385
0.3-0.4	7529
0.4-0.5	9752
0.5-0.6	5291
0.6-0.7	5054
0.7-0.8	6364
0.8-0.85	2727
0.85-0.9	545
0.9-0.95	58
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC298778
0.9636	High Similarity	NPC68381
0.9576	High Similarity	NPC472054
0.9515	High Similarity	NPC5029
0.9515	High Similarity	NPC111536
0.9515	High Similarity	NPC30432
0.9515	High Similarity	NPC271385
0.9515	High Similarity	NPC76128
0.9512	High Similarity	NPC259905
0.9509	High Similarity	NPC178851
0.9467	High Similarity	NPC293227
0.9467	High Similarity	NPC473631
0.9467	High Similarity	NPC473717
0.9467	High Similarity	NPC475662
0.9408	High Similarity	NPC477860
0.9408	High Similarity	NPC475161
0.9401	High Similarity	NPC199533
0.9401	High Similarity	NPC63105
0.9401	High Similarity	NPC470454
0.9357	High Similarity	NPC473686
0.9357	High Similarity	NPC475220
0.9357	High Similarity	NPC221140
0.9357	High Similarity	NPC475352
0.9357	High Similarity	NPC229817
0.9345	High Similarity	NPC475246
0.9345	High Similarity	NPC475233
0.9345	High Similarity	NPC46958
0.9341	High Similarity	NPC213052
0.9286	High Similarity	NPC3718
0.9277	High Similarity	NPC222455
0.9235	High Similarity	NPC277710
0.9235	High Similarity	NPC245059
0.9235	High Similarity	NPC153578
0.9235	High Similarity	NPC114257
0.9235	High Similarity	NPC212290
0.9235	High Similarity	NPC299149
0.9235	High Similarity	NPC84494
0.9226	High Similarity	NPC98776
0.9217	High Similarity	NPC249977
0.9212	High Similarity	NPC7752
0.9207	High Similarity	NPC216752
0.9205	High Similarity	NPC470193
0.9205	High Similarity	NPC470198
0.9205	High Similarity	NPC470194
0.9205	High Similarity	NPC470197
0.9205	High Similarity	NPC470196
0.9205	High Similarity	NPC470200
0.9205	High Similarity	NPC470195
0.9205	High Similarity	NPC282474
0.9205	High Similarity	NPC316274
0.9191	High Similarity	NPC105591
0.9181	High Similarity	NPC470453
0.9181	High Similarity	NPC315221
0.9181	High Similarity	NPC470452
0.9181	High Similarity	NPC164047
0.9181	High Similarity	NPC470448
0.9172	High Similarity	NPC146803
0.9162	High Similarity	NPC473202
0.9128	High Similarity	NPC313452
0.9096	High Similarity	NPC178281
0.9091	High Similarity	NPC470199
0.9091	High Similarity	NPC314459
0.9085	High Similarity	NPC328093
0.9048	High Similarity	NPC191653
0.9024	High Similarity	NPC308265
0.9023	High Similarity	NPC87583
0.9018	High Similarity	NPC283480
0.9018	High Similarity	NPC127406
0.9018	High Similarity	NPC261866
0.9018	High Similarity	NPC148323
0.9006	High Similarity	NPC324220
0.9006	High Similarity	NPC312630
0.9	High Similarity	NPC85368
0.9	High Similarity	NPC199357
0.8994	High Similarity	NPC76047
0.8994	High Similarity	NPC477571
0.8994	High Similarity	NPC241874
0.8994	High Similarity	NPC477573
0.8994	High Similarity	NPC477572
0.8988	High Similarity	NPC477502
0.8982	High Similarity	NPC475979
0.8982	High Similarity	NPC294722
0.8982	High Similarity	NPC99216
0.8976	High Similarity	NPC131745
0.8976	High Similarity	NPC101116
0.8976	High Similarity	NPC44947
0.8976	High Similarity	NPC278329
0.8976	High Similarity	NPC259834
0.8976	High Similarity	NPC212099
0.8976	High Similarity	NPC146837
0.897	High Similarity	NPC472055
0.897	High Similarity	NPC470358
0.897	High Similarity	NPC472320
0.897	High Similarity	NPC271479
0.8963	High Similarity	NPC43638
0.8963	High Similarity	NPC23817
0.8957	High Similarity	NPC470603
0.8957	High Similarity	NPC470604
0.8957	High Similarity	NPC192219
0.8957	High Similarity	NPC470605
0.8957	High Similarity	NPC82190
0.8957	High Similarity	NPC174599
0.8953	High Similarity	NPC469600
0.8922	High Similarity	NPC278419
0.8922	High Similarity	NPC124155
0.8922	High Similarity	NPC179198
0.8922	High Similarity	NPC257566
0.8922	High Similarity	NPC66087
0.8922	High Similarity	NPC183672
0.8916	High Similarity	NPC47923
0.8914	High Similarity	NPC241847
0.8909	High Similarity	NPC73511
0.8909	High Similarity	NPC43761
0.8909	High Similarity	NPC470339
0.8902	High Similarity	NPC206378
0.8896	High Similarity	NPC211158
0.8896	High Similarity	NPC205172
0.8896	High Similarity	NPC78021
0.8896	High Similarity	NPC106625
0.8896	High Similarity	NPC87304
0.8896	High Similarity	NPC185103
0.8896	High Similarity	NPC268950
0.8896	High Similarity	NPC108706
0.8896	High Similarity	NPC209393
0.8889	High Similarity	NPC190217
0.8882	High Similarity	NPC150767
0.8882	High Similarity	NPC210808
0.8882	High Similarity	NPC78734
0.8882	High Similarity	NPC199079
0.8876	High Similarity	NPC474024
0.8876	High Similarity	NPC298847
0.8876	High Similarity	NPC472622
0.887	High Similarity	NPC314672
0.8862	High Similarity	NPC97637
0.8862	High Similarity	NPC190450
0.8862	High Similarity	NPC472876
0.8862	High Similarity	NPC187934
0.8862	High Similarity	NPC300537
0.8862	High Similarity	NPC127782
0.8862	High Similarity	NPC473043
0.8855	High Similarity	NPC470810
0.8851	High Similarity	NPC208069
0.8851	High Similarity	NPC265795
0.8848	High Similarity	NPC208651
0.8848	High Similarity	NPC257309
0.8848	High Similarity	NPC161749
0.8848	High Similarity	NPC197896
0.8848	High Similarity	NPC206641
0.8848	High Similarity	NPC313163
0.8848	High Similarity	NPC258035
0.8848	High Similarity	NPC470606
0.8848	High Similarity	NPC156457
0.8841	High Similarity	NPC39351
0.8841	High Similarity	NPC26195
0.8841	High Similarity	NPC27408
0.8841	High Similarity	NPC99233
0.8841	High Similarity	NPC95090
0.8841	High Similarity	NPC72649
0.8841	High Similarity	NPC97052
0.8841	High Similarity	NPC169248
0.8837	High Similarity	NPC469601
0.8837	High Similarity	NPC470667
0.8834	High Similarity	NPC273483
0.8834	High Similarity	NPC259182
0.8834	High Similarity	NPC87708
0.8834	High Similarity	NPC121001
0.883	High Similarity	NPC257011
0.883	High Similarity	NPC137871
0.883	High Similarity	NPC67134
0.883	High Similarity	NPC9002
0.883	High Similarity	NPC288152
0.883	High Similarity	NPC472386
0.883	High Similarity	NPC256760
0.883	High Similarity	NPC47140
0.8827	High Similarity	NPC214454
0.8827	High Similarity	NPC477240
0.8827	High Similarity	NPC106025
0.8824	High Similarity	NPC470206
0.8824	High Similarity	NPC470207
0.882	High Similarity	NPC48474
0.882	High Similarity	NPC264302
0.8817	High Similarity	NPC5778
0.8817	High Similarity	NPC207575
0.8817	High Similarity	NPC236934
0.8817	High Similarity	NPC13481
0.8817	High Similarity	NPC70441
0.8817	High Similarity	NPC472621
0.881	High Similarity	NPC309025
0.881	High Similarity	NPC243930
0.881	High Similarity	NPC222936
0.881	High Similarity	NPC121703
0.881	High Similarity	NPC19709
0.881	High Similarity	NPC88023
0.881	High Similarity	NPC284960
0.881	High Similarity	NPC29830
0.8802	High Similarity	NPC477629
0.8802	High Similarity	NPC159579
0.8802	High Similarity	NPC48093
0.8802	High Similarity	NPC101636
0.8802	High Similarity	NPC216496

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 NPC474345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	932
0.2-0.3	1830
0.3-0.4	2598
0.4-0.5	1892
0.5-0.6	980
0.6-0.7	372
0.7-0.8	150
0.8-0.85	43
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8848	High Similarity	NPD4381	Clinical (unspecified phase)
0.8779	High Similarity	NPD6559	Discontinued
0.8713	High Similarity	NPD7804	Clinical (unspecified phase)
0.869	High Similarity	NPD6959	Discontinued
0.8678	High Similarity	NPD8312	Approved
0.8678	High Similarity	NPD8313	Approved
0.8663	High Similarity	NPD7074	Phase 3
0.8652	High Similarity	NPD7879	Clinical (unspecified phase)
0.8614	High Similarity	NPD8443	Clinical (unspecified phase)
0.8605	High Similarity	NPD7054	Approved
0.8555	High Similarity	NPD7472	Approved
0.8554	High Similarity	NPD7819	Suspended
0.8545	High Similarity	NPD7411	Suspended
0.8514	High Similarity	NPD4338	Clinical (unspecified phase)
0.8512	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD6797	Phase 2
0.8497	Intermediate Similarity	NPD5844	Phase 1
0.8488	Intermediate Similarity	NPD7473	Discontinued
0.8485	Intermediate Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD7251	Discontinued
0.8443	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD3818	Discontinued
0.8421	Intermediate Similarity	NPD6232	Discontinued
0.8409	Intermediate Similarity	NPD7808	Phase 3
0.8343	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6166	Phase 2
0.8324	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD1934	Approved
0.8274	Intermediate Similarity	NPD6801	Discontinued
0.8263	Intermediate Similarity	NPD8151	Discontinued
0.8229	Intermediate Similarity	NPD7228	Approved
0.8204	Intermediate Similarity	NPD3226	Approved
0.8191	Intermediate Similarity	NPD7435	Discontinued
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD2533	Approved
0.8166	Intermediate Similarity	NPD37	Approved
0.814	Intermediate Similarity	NPD6234	Discontinued
0.8129	Intermediate Similarity	NPD4965	Approved
0.8129	Intermediate Similarity	NPD4966	Approved
0.8129	Intermediate Similarity	NPD4967	Phase 2
0.8128	Intermediate Similarity	NPD6777	Approved
0.8128	Intermediate Similarity	NPD6778	Approved
0.8128	Intermediate Similarity	NPD6776	Approved
0.8128	Intermediate Similarity	NPD6779	Approved
0.8128	Intermediate Similarity	NPD6781	Approved
0.8128	Intermediate Similarity	NPD6782	Approved
0.8128	Intermediate Similarity	NPD6780	Approved
0.8083	Intermediate Similarity	NPD7783	Phase 2
0.8083	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3817	Phase 2
0.8047	Intermediate Similarity	NPD6599	Discontinued
0.8046	Intermediate Similarity	NPD7199	Phase 2
0.8037	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD5402	Approved
0.7964	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7874	Approved
0.7927	Intermediate Similarity	NPD1549	Phase 2
0.7919	Intermediate Similarity	NPD7768	Phase 2
0.7907	Intermediate Similarity	NPD8455	Phase 2
0.7907	Intermediate Similarity	NPD1465	Phase 2
0.7907	Intermediate Similarity	NPD2801	Approved
0.7906	Intermediate Similarity	NPD7697	Approved
0.7906	Intermediate Similarity	NPD7696	Phase 3
0.7906	Intermediate Similarity	NPD7698	Approved
0.7904	Intermediate Similarity	NPD6799	Approved
0.7882	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7458	Discontinued
0.7879	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD5403	Approved
0.7865	Intermediate Similarity	NPD8320	Phase 1
0.7865	Intermediate Similarity	NPD8319	Approved
0.7865	Intermediate Similarity	NPD7870	Phase 2
0.7865	Intermediate Similarity	NPD7871	Phase 2
0.7861	Intermediate Similarity	NPD6535	Approved
0.7861	Intermediate Similarity	NPD6534	Approved
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6823	Phase 2
0.7845	Intermediate Similarity	NPD7240	Approved
0.7835	Intermediate Similarity	NPD7701	Phase 2
0.7831	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD4628	Phase 3
0.7826	Intermediate Similarity	NPD8150	Discontinued
0.7821	Intermediate Similarity	NPD3751	Discontinued
0.7806	Intermediate Similarity	NPD7801	Approved
0.7798	Intermediate Similarity	NPD7390	Discontinued
0.7798	Intermediate Similarity	NPD1511	Approved
0.7797	Intermediate Similarity	NPD3787	Discontinued
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2346	Discontinued
0.7751	Intermediate Similarity	NPD5401	Approved
0.7751	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7699	Phase 2
0.7737	Intermediate Similarity	NPD7700	Phase 2
0.7714	Intermediate Similarity	NPD3882	Suspended
0.7706	Intermediate Similarity	NPD1512	Approved
0.7697	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD5711	Approved
0.7697	Intermediate Similarity	NPD5710	Approved
0.7665	Intermediate Similarity	NPD6674	Discontinued
0.7661	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1510	Phase 2
0.7636	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1607	Approved
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6213	Phase 3
0.7619	Intermediate Similarity	NPD6212	Phase 3
0.7619	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7584	Approved
0.759	Intermediate Similarity	NPD6099	Approved
0.759	Intermediate Similarity	NPD6100	Approved
0.759	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD1551	Phase 2
0.7554	Intermediate Similarity	NPD7685	Pre-registration
0.7549	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8434	Phase 2
0.753	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2800	Approved
0.7426	Intermediate Similarity	NPD7930	Approved
0.7425	Intermediate Similarity	NPD2799	Discontinued
0.7423	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5953	Discontinued
0.7403	Intermediate Similarity	NPD7229	Phase 3
0.7399	Intermediate Similarity	NPD6273	Approved
0.7387	Intermediate Similarity	NPD7585	Approved
0.7385	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5405	Approved
0.7381	Intermediate Similarity	NPD5406	Approved
0.7381	Intermediate Similarity	NPD5404	Approved
0.7381	Intermediate Similarity	NPD5408	Approved
0.7378	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD920	Approved
0.7353	Intermediate Similarity	NPD1243	Approved
0.7341	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7583	Approved
0.7333	Intermediate Similarity	NPD919	Approved
0.7333	Intermediate Similarity	NPD8285	Discontinued
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7003	Approved
0.7306	Intermediate Similarity	NPD4363	Phase 3
0.7306	Intermediate Similarity	NPD4360	Phase 2
0.7305	Intermediate Similarity	NPD6651	Approved
0.7297	Intermediate Similarity	NPD7286	Phase 2
0.7289	Intermediate Similarity	NPD4060	Phase 1
0.7286	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7256	Intermediate Similarity	NPD4908	Phase 1
0.7253	Intermediate Similarity	NPD1247	Approved
0.7246	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5124	Phase 1
0.7243	Intermediate Similarity	NPD7177	Discontinued
0.7241	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7266	Discontinued
0.7225	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4625	Phase 3
0.7204	Intermediate Similarity	NPD8059	Phase 3
0.7204	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2438	Suspended
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7158	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8127	Discontinued
0.7151	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7114	Intermediate Similarity	NPD7999	Approved
0.7081	Intermediate Similarity	NPD3926	Phase 2
0.7069	Intermediate Similarity	NPD6190	Approved
0.7066	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD7799	Discontinued
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7059	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8366	Approved
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7042	Intermediate Similarity	NPD8469	Approved
0.7041	Intermediate Similarity	NPD6355	Discontinued

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