NPASS Compound

Structure

NPC178281 OpenBabel07101718272D 33 36 0 0 1 0 0 0 0 0999 V2000 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 4.3301 -1.5000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 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 3.4641 1.0000 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 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 6.0622 -0.5000 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 2.5981 1.5000 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 1.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 31 1 0 0 0 0 10 24 2 0 0 0 0 10 31 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 32 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 33 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 26 2 0 0 0 0 19 21 1 0 0 0 0 19 27 1 6 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.12
Volume:	436.312
LogP:	2.295
LogD:	1.66
LogS:	-4.76
# Rotatable Bonds:	5
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	3.846
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828
MDCK Permeability:	3.126462979707867e-05
Pgp-inhibitor:	0.597
Pgp-substrate:	0.425
Human Intestinal Absorption (HIA):	0.72
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	88.77381134033203%
Volume Distribution (VD):	0.697
Pgp-substrate:	5.164867401123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.536
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	2.177
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.923
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.137
Carcinogencity:	0.878
Eye Corrosion:	0.003
Eye Irritation:	0.651
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC178281

Natural Product ID:	NPC178281
*Common Name:**	Chrysophanol-8-O-Beta-D-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(8-hydroxy-6-methyl-9,10-dioxoanthracen-1-yl)oxyoxan-2-yl]methyl acetate
Synonyms:
Standard InCHIKey:	YXXRVZXJNUVIJO-UGPBBDQXSA-N
Standard InCHI:	InChI=1S/C23H22O10/c1-9-6-12-16(13(25)7-9)20(28)17-11(18(12)26)4-3-5-14(17)32-23-22(30)21(29)19(27)15(33-23)8-31-10(2)24/h3-7,15,19,21-23,25,27,29-30H,8H2,1-2H3/t15-,19-,21+,22-,23-/m1/s1
SMILES:	Cc1cc2c(c(c1)O)C(=O)c1c(cccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O1)O)O)O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204400
PubChem CID:	71452247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO32783	endophytic aspergillus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23683594]
NPO32491	rumex plants	n.a.	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23683594]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	4100.0	nM	PMID[575318]

☑ 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 NPC178281 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	360
0.1-0.2	1445
0.2-0.3	3063
0.3-0.4	6892
0.4-0.5	10251
0.5-0.6	5594
0.6-0.7	5751
0.7-0.8	7867
0.8-0.85	1226
0.85-0.9	184
0.9-0.95	59
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC146837
0.9871	High Similarity	NPC278329
0.9744	High Similarity	NPC101116
0.9744	High Similarity	NPC212099
0.95	High Similarity	NPC63470
0.9448	High Similarity	NPC68381
0.9387	High Similarity	NPC199357
0.9387	High Similarity	NPC85368
0.9387	High Similarity	NPC203751
0.9337	High Similarity	NPC477860
0.9337	High Similarity	NPC475161
0.9329	High Similarity	NPC470667
0.9329	High Similarity	NPC186800
0.9325	High Similarity	NPC5029
0.9325	High Similarity	NPC76128
0.9325	High Similarity	NPC111536
0.9325	High Similarity	NPC30432
0.9325	High Similarity	NPC271385
0.9321	High Similarity	NPC246274
0.9273	High Similarity	NPC102053
0.9273	High Similarity	NPC289876
0.9273	High Similarity	NPC475246
0.9273	High Similarity	NPC170018
0.9273	High Similarity	NPC92403
0.9273	High Similarity	NPC76112
0.9273	High Similarity	NPC66820
0.9264	High Similarity	NPC298778
0.925	High Similarity	NPC216752
0.9241	High Similarity	NPC208651
0.9241	High Similarity	NPC206641
0.9212	High Similarity	NPC3718
0.9212	High Similarity	NPC307754
0.9212	High Similarity	NPC223735
0.9207	High Similarity	NPC315619
0.9202	High Similarity	NPC222455
0.9193	High Similarity	NPC17432
0.9177	High Similarity	NPC283480
0.9177	High Similarity	NPC148323
0.9162	High Similarity	NPC153578
0.9162	High Similarity	NPC114257
0.9162	High Similarity	NPC277710
0.9162	High Similarity	NPC299149
0.9162	High Similarity	NPC58538
0.9157	High Similarity	NPC475233
0.9157	High Similarity	NPC46958
0.9152	High Similarity	NPC472054
0.913	High Similarity	NPC97637
0.913	High Similarity	NPC187934
0.9119	High Similarity	NPC177742
0.9118	High Similarity	NPC105591
0.9114	High Similarity	NPC82190
0.9114	High Similarity	NPC174599
0.9114	High Similarity	NPC3449
0.9114	High Similarity	NPC192219
0.9107	High Similarity	NPC197357
0.9107	High Similarity	NPC85316
0.9096	High Similarity	NPC474345
0.9064	High Similarity	NPC205721
0.9051	High Similarity	NPC209393
0.9051	High Similarity	NPC205172
0.9051	High Similarity	NPC185103
0.9048	High Similarity	NPC212290
0.9042	High Similarity	NPC314489
0.9042	High Similarity	NPC232818
0.9042	High Similarity	NPC198893
0.9036	High Similarity	NPC98776
0.9018	High Similarity	NPC478022
0.9018	High Similarity	NPC478020
0.9006	High Similarity	NPC328093
0.9	High Similarity	NPC224557
0.9	High Similarity	NPC292706
0.8982	High Similarity	NPC146803
0.8982	High Similarity	NPC470454
0.8982	High Similarity	NPC199533
0.897	High Similarity	NPC259905
0.8963	High Similarity	NPC178851
0.8947	High Similarity	NPC87583
0.8944	High Similarity	NPC53139
0.8931	High Similarity	NPC474622
0.8931	High Similarity	NPC230439
0.8931	High Similarity	NPC92153
0.8931	High Similarity	NPC474621
0.8931	High Similarity	NPC279281
0.8931	High Similarity	NPC299761
0.8902	High Similarity	NPC99216
0.8902	High Similarity	NPC314672
0.8896	High Similarity	NPC61594
0.8896	High Similarity	NPC56735
0.8869	High Similarity	NPC193377
0.8869	High Similarity	NPC63105
0.8868	High Similarity	NPC215811
0.8868	High Similarity	NPC474534
0.8868	High Similarity	NPC474533
0.8862	High Similarity	NPC183441
0.8855	High Similarity	NPC191653
0.8841	High Similarity	NPC147596
0.8837	High Similarity	NPC241847
0.883	High Similarity	NPC293227
0.883	High Similarity	NPC473631
0.883	High Similarity	NPC475662
0.883	High Similarity	NPC473717
0.8827	High Similarity	NPC231475
0.8827	High Similarity	NPC57072
0.8824	High Similarity	NPC84494
0.8824	High Similarity	NPC245059
0.8812	High Similarity	NPC470331
0.881	High Similarity	NPC213052
0.8805	High Similarity	NPC39819
0.8802	High Similarity	NPC241874
0.8802	High Similarity	NPC478021
0.8802	High Similarity	NPC52598
0.8795	High Similarity	NPC298847
0.878	High Similarity	NPC22324
0.8772	High Similarity	NPC164047
0.8772	High Similarity	NPC470448
0.8772	High Similarity	NPC470452
0.8772	High Similarity	NPC315221
0.8772	High Similarity	NPC470453
0.875	High Similarity	NPC294501
0.875	High Similarity	NPC312006
0.875	High Similarity	NPC471921
0.875	High Similarity	NPC129930
0.875	High Similarity	NPC471920
0.875	High Similarity	NPC474075
0.875	High Similarity	NPC20114
0.875	High Similarity	NPC114550
0.875	High Similarity	NPC471922
0.875	High Similarity	NPC292712
0.8742	High Similarity	NPC93619
0.8728	High Similarity	NPC221140
0.8728	High Similarity	NPC473686
0.8728	High Similarity	NPC475220
0.8728	High Similarity	NPC229817
0.8728	High Similarity	NPC475352
0.8721	High Similarity	NPC313452
0.872	High Similarity	NPC132737
0.8706	High Similarity	NPC176246
0.8696	High Similarity	NPC299435
0.8696	High Similarity	NPC260604
0.869	High Similarity	NPC76047
0.8683	High Similarity	NPC249977
0.8679	High Similarity	NPC70764
0.8675	High Similarity	NPC7752
0.8675	High Similarity	NPC280923
0.8675	High Similarity	NPC474301
0.8675	High Similarity	NPC478026
0.8671	High Similarity	NPC83975
0.8671	High Similarity	NPC4958
0.8671	High Similarity	NPC140722
0.8671	High Similarity	NPC92054
0.8663	High Similarity	NPC208069
0.8659	High Similarity	NPC472320
0.8655	High Similarity	NPC47191
0.865	High Similarity	NPC23817
0.865	High Similarity	NPC474441
0.865	High Similarity	NPC29552
0.865	High Similarity	NPC474401
0.865	High Similarity	NPC474398
0.865	High Similarity	NPC43638
0.865	High Similarity	NPC476026
0.8636	High Similarity	NPC48474
0.8636	High Similarity	NPC264302
0.8634	High Similarity	NPC473967
0.8634	High Similarity	NPC183536
0.8634	High Similarity	NPC34965
0.8634	High Similarity	NPC281272
0.8631	High Similarity	NPC473202
0.8625	High Similarity	NPC473966
0.8623	High Similarity	NPC178173
0.8614	High Similarity	NPC127415
0.8613	High Similarity	NPC478001
0.8613	High Similarity	NPC476203
0.8608	High Similarity	NPC285122
0.8599	High Similarity	NPC103910
0.8598	High Similarity	NPC43761
0.8598	High Similarity	NPC73511
0.8596	High Similarity	NPC475054
0.8596	High Similarity	NPC312630
0.8596	High Similarity	NPC324220
0.8589	High Similarity	NPC127406
0.8588	High Similarity	NPC154986
0.8588	High Similarity	NPC172033
0.8588	High Similarity	NPC65118
0.8588	High Similarity	NPC175230
0.8588	High Similarity	NPC316539
0.8588	High Similarity	NPC88560
0.858	High Similarity	NPC149011
0.858	High Similarity	NPC204937
0.858	High Similarity	NPC313304
0.8571	High Similarity	NPC103633
0.8571	High Similarity	NPC116745
0.8563	High Similarity	NPC231254
0.8556	High Similarity	NPC131405
0.8554	High Similarity	NPC44947
0.8554	High Similarity	NPC131745
0.8554	High Similarity	NPC472876
0.8554	High Similarity	NPC259834
0.8554	High Similarity	NPC473961
0.8553	High Similarity	NPC302989
0.8553	High Similarity	NPC71055

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 NPC178281 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	875
0.2-0.3	1612
0.3-0.4	2526
0.4-0.5	2061
0.5-0.6	1105
0.6-0.7	461
0.7-0.8	155
0.8-0.85	36
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9273	High Similarity	NPD8312	Approved
0.9273	High Similarity	NPD8313	Approved
0.8895	High Similarity	NPD7879	Clinical (unspecified phase)
0.8698	High Similarity	NPD6559	Discontinued
0.8679	High Similarity	NPD3226	Approved
0.8537	High Similarity	NPD4381	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2346	Discontinued
0.8407	Intermediate Similarity	NPD7435	Discontinued
0.8352	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6779	Approved
0.8343	Intermediate Similarity	NPD6780	Approved
0.8343	Intermediate Similarity	NPD6777	Approved
0.8343	Intermediate Similarity	NPD6782	Approved
0.8343	Intermediate Similarity	NPD6778	Approved
0.8343	Intermediate Similarity	NPD6776	Approved
0.8343	Intermediate Similarity	NPD6781	Approved
0.8304	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8246	Intermediate Similarity	NPD3818	Discontinued
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8221	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7075	Discontinued
0.8198	Intermediate Similarity	NPD7054	Approved
0.8198	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD5402	Approved
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8171	Intermediate Similarity	NPD4380	Phase 2
0.8166	Intermediate Similarity	NPD6959	Discontinued
0.8152	Intermediate Similarity	NPD6823	Phase 2
0.815	Intermediate Similarity	NPD7472	Approved
0.8138	Intermediate Similarity	NPD7874	Approved
0.8138	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD8455	Phase 2
0.8108	Intermediate Similarity	NPD7696	Phase 3
0.8108	Intermediate Similarity	NPD7698	Approved
0.8108	Intermediate Similarity	NPD7697	Approved
0.8103	Intermediate Similarity	NPD6797	Phase 2
0.8085	Intermediate Similarity	NPD8151	Discontinued
0.8066	Intermediate Similarity	NPD6534	Approved
0.8066	Intermediate Similarity	NPD6535	Approved
0.8065	Intermediate Similarity	NPD7870	Phase 2
0.8065	Intermediate Similarity	NPD7871	Phase 2
0.8057	Intermediate Similarity	NPD7251	Discontinued
0.8036	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD8150	Discontinued
0.8032	Intermediate Similarity	NPD7701	Phase 2
0.8024	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8011	Intermediate Similarity	NPD6213	Phase 3
0.8011	Intermediate Similarity	NPD6212	Phase 3
0.8011	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD7783	Phase 2
0.8	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7968	Intermediate Similarity	NPD8320	Phase 1
0.7968	Intermediate Similarity	NPD8319	Approved
0.7964	Intermediate Similarity	NPD6801	Discontinued
0.795	Intermediate Similarity	NPD4628	Phase 3
0.7935	Intermediate Similarity	NPD7700	Phase 2
0.7935	Intermediate Similarity	NPD7699	Phase 2
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7931	Intermediate Similarity	NPD7228	Approved
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD7801	Approved
0.7892	Intermediate Similarity	NPD7458	Discontinued
0.787	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD1934	Approved
0.784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6234	Discontinued
0.7824	Intermediate Similarity	NPD4966	Approved
0.7824	Intermediate Similarity	NPD4967	Phase 2
0.7824	Intermediate Similarity	NPD4965	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7821	Intermediate Similarity	NPD2313	Discontinued
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2532	Approved
0.7758	Intermediate Similarity	NPD2533	Approved
0.7758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2799	Discontinued
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.773	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1551	Phase 2
0.7701	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5494	Approved
0.7674	Intermediate Similarity	NPD3749	Approved
0.7669	Intermediate Similarity	NPD6674	Discontinued
0.7661	Intermediate Similarity	NPD3817	Phase 2
0.7654	Intermediate Similarity	NPD7685	Pre-registration
0.7651	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD1470	Approved
0.7607	Intermediate Similarity	NPD1549	Phase 2
0.7605	Intermediate Similarity	NPD6273	Approved
0.7602	Intermediate Similarity	NPD2801	Approved
0.7602	Intermediate Similarity	NPD1465	Phase 2
0.7593	Intermediate Similarity	NPD5408	Approved
0.7593	Intermediate Similarity	NPD5405	Approved
0.7593	Intermediate Similarity	NPD5404	Approved
0.7593	Intermediate Similarity	NPD5406	Approved
0.759	Intermediate Similarity	NPD6799	Approved
0.7562	Intermediate Similarity	NPD1933	Approved
0.7556	Intermediate Similarity	NPD7240	Approved
0.7546	Intermediate Similarity	NPD7266	Discontinued
0.7546	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7528	Intermediate Similarity	NPD7177	Discontinued
0.7515	Intermediate Similarity	NPD7003	Approved
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3882	Suspended
0.7513	Intermediate Similarity	NPD8285	Discontinued
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7461	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD447	Suspended
0.7452	Intermediate Similarity	NPD2798	Approved
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4060	Phase 1
0.7389	Intermediate Similarity	NPD1203	Approved
0.7381	Intermediate Similarity	NPD1511	Approved
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2796	Approved
0.7375	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8059	Phase 3
0.7366	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7097	Phase 1
0.736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1201	Approved
0.7355	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8127	Discontinued
0.7341	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD7584	Approved
0.7317	Intermediate Similarity	NPD4308	Phase 3
0.7317	Intermediate Similarity	NPD1510	Phase 2
0.7317	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD5711	Approved
0.7301	Intermediate Similarity	NPD1607	Approved
0.7294	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD7930	Approved
0.7244	Intermediate Similarity	NPD1091	Approved
0.7229	Intermediate Similarity	NPD5763	Approved
0.7229	Intermediate Similarity	NPD2344	Approved
0.7229	Intermediate Similarity	NPD5762	Approved
0.7225	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4625	Phase 3
0.7197	Intermediate Similarity	NPD9717	Approved
0.7178	Intermediate Similarity	NPD1240	Approved
0.717	Intermediate Similarity	NPD2797	Approved
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD7985	Registered
0.716	Intermediate Similarity	NPD3268	Approved
0.7151	Intermediate Similarity	NPD920	Approved
0.715	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7799	Discontinued
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7126	Intermediate Similarity	NPD6002	Phase 3
0.7126	Intermediate Similarity	NPD6005	Phase 3
0.7126	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6004	Phase 3
0.7121	Intermediate Similarity	NPD7585	Approved
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7107	Intermediate Similarity	NPD7999	Approved
0.7107	Intermediate Similarity	NPD1283	Approved
0.7104	Intermediate Similarity	NPD7286	Phase 2
0.7092	Intermediate Similarity	NPD7680	Approved
0.7089	Intermediate Similarity	NPD1608	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