NPASS Compound

Structure

NPC82190 OpenBabel07101718242D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -1.7321 3.0000 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 -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 -0.0000 -5.0000 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 -1.7321 1.0000 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 -2.5981 2.5000 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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 -3.4641 -0.0000 0.0000 C 0 0 0 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 -0.8660 -1.5000 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 -0.0000 -2.0000 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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -4.3301 1.5000 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 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 0.0000 -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 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 18 1 0 0 0 0 14 26 1 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 12 1 6 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 20 29 2 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 34 1 1 0 0 0 24 33 1 6 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.16
Volume:	462.114
LogP:	3.994
LogD:	2.248
LogS:	-3.598
# Rotatable Bonds:	4
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	4.394
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.046
MDCK Permeability:	6.376111286954256e-06
Pgp-inhibitor:	0.018
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.729
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	96.77274322509766%
Volume Distribution (VD):	0.476
Pgp-substrate:	6.694372177124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.695
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	2.216
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.946
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.746
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC82190

Natural Product ID:	NPC82190
*Common Name:**	Alvaradoin M
IUPAC Name:	[(2R,3S,4R,5R,6S)-2-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,5,6-trihydroxyoxan-4-yl] 3-methylbut-2-enoate
Synonyms:	alvaradoin M
Standard InCHIKey:	XVEVCPOACUOIOH-RUSJTPRDSA-N
Standard InCHI:	InChI=1S/C25H26O9/c1-10(2)7-16(28)33-24-21(30)23(34-25(32)22(24)31)17-12-5-4-6-14(26)18(12)20(29)19-13(17)8-11(3)9-15(19)27/h4-9,17,21-27,30-32H,1-3H3/t17-,21-,22+,23+,24+,25-/m0/s1
SMILES:	CC(=CC(=O)O[C@@H]1[C@H]([C@@H]([C@H]2c3cccc(c3C(=O)c3c2cc(C)cc3O)O)O[C@@H]([C@@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229684
PubChem CID:	44424604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO30060	Alvaradoa haitiensis	Species	Picramniaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17552563]
NPO30060	Alvaradoa haitiensis	Species	Picramniaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17552563]

☑ 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
EC50	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	EC50	=	380.0	nM	PMID[539041]

☑ 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 NPC82190 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	336
0.1-0.2	1249
0.2-0.3	2734
0.3-0.4	5771
0.4-0.5	10140
0.5-0.6	7533
0.6-0.7	6561
0.7-0.8	7647
0.8-0.85	583
0.85-0.9	115
0.9-0.95	16
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC174599
1.0	High Similarity	NPC192219
0.9932	High Similarity	NPC148323
0.9932	High Similarity	NPC283480
0.9797	High Similarity	NPC209393
0.9797	High Similarity	NPC205172
0.9733	High Similarity	NPC208651
0.9733	High Similarity	NPC206641
0.9608	High Similarity	NPC187934
0.9608	High Similarity	NPC97637
0.96	High Similarity	NPC3449
0.9539	High Similarity	NPC53139
0.9388	High Similarity	NPC170055
0.932	High Similarity	NPC300684
0.932	High Similarity	NPC84568
0.932	High Similarity	NPC218866
0.932	High Similarity	NPC48130
0.9211	High Similarity	NPC474534
0.9211	High Similarity	NPC474533
0.9195	High Similarity	NPC285122
0.9114	High Similarity	NPC478020
0.9114	High Similarity	NPC478022
0.9114	High Similarity	NPC178281
0.9026	High Similarity	NPC474621
0.9026	High Similarity	NPC474622
0.9006	High Similarity	NPC298778
0.8987	High Similarity	NPC278329
0.8987	High Similarity	NPC216752
0.8987	High Similarity	NPC212099
0.8987	High Similarity	NPC146837
0.8987	High Similarity	NPC101116
0.8957	High Similarity	NPC474345
0.8951	High Similarity	NPC183441
0.8896	High Similarity	NPC472054
0.8889	High Similarity	NPC478021
0.8841	High Similarity	NPC470667
0.8841	High Similarity	NPC68381
0.8834	High Similarity	NPC294501
0.8797	High Similarity	NPC314795
0.8788	High Similarity	NPC176246
0.878	High Similarity	NPC199357
0.878	High Similarity	NPC203751
0.878	High Similarity	NPC85368
0.8758	High Similarity	NPC478026
0.8743	High Similarity	NPC475161
0.8743	High Similarity	NPC477860
0.8742	High Similarity	NPC328093
0.8734	High Similarity	NPC257309
0.8727	High Similarity	NPC186800
0.872	High Similarity	NPC271385
0.872	High Similarity	NPC5029
0.872	High Similarity	NPC76128
0.872	High Similarity	NPC111536
0.872	High Similarity	NPC30432
0.8718	High Similarity	NPC257847
0.8712	High Similarity	NPC259905
0.8704	High Similarity	NPC469419
0.8704	High Similarity	NPC178851
0.8701	High Similarity	NPC94781
0.8693	High Similarity	NPC120536
0.869	High Similarity	NPC473631
0.869	High Similarity	NPC475662
0.869	High Similarity	NPC293227
0.869	High Similarity	NPC473717
0.8684	High Similarity	NPC103910
0.8675	High Similarity	NPC289876
0.8675	High Similarity	NPC102053
0.8675	High Similarity	NPC76112
0.8675	High Similarity	NPC475246
0.8675	High Similarity	NPC170018
0.8675	High Similarity	NPC66820
0.8675	High Similarity	NPC92403
0.8671	High Similarity	NPC478027
0.8667	High Similarity	NPC65118
0.8662	High Similarity	NPC218870
0.8662	High Similarity	NPC474824
0.8662	High Similarity	NPC470408
0.8662	High Similarity	NPC182921
0.865	High Similarity	NPC63470
0.8645	High Similarity	NPC247219
0.8645	High Similarity	NPC280753
0.8645	High Similarity	NPC44378
0.8642	High Similarity	NPC470735
0.8642	High Similarity	NPC329647
0.8642	High Similarity	NPC99216
0.8636	High Similarity	NPC471734
0.8625	High Similarity	NPC208676
0.8625	High Similarity	NPC130489
0.8616	High Similarity	NPC29552
0.8614	High Similarity	NPC3718
0.8614	High Similarity	NPC470454
0.8614	High Similarity	NPC63105
0.8614	High Similarity	NPC199533
0.8608	High Similarity	NPC266469
0.8608	High Similarity	NPC472835
0.8598	High Similarity	NPC246274
0.8598	High Similarity	NPC222455
0.8598	High Similarity	NPC175477
0.859	High Similarity	NPC475407
0.8588	High Similarity	NPC473686
0.8588	High Similarity	NPC221140
0.8588	High Similarity	NPC229817
0.8588	High Similarity	NPC475352
0.8588	High Similarity	NPC475220
0.858	High Similarity	NPC17432
0.8571	High Similarity	NPC114257
0.8571	High Similarity	NPC277710
0.8571	High Similarity	NPC58538
0.8571	High Similarity	NPC477627
0.8571	High Similarity	NPC153578
0.8571	High Similarity	NPC471735
0.8571	High Similarity	NPC299149
0.8563	High Similarity	NPC46958
0.8563	High Similarity	NPC475233
0.8554	High Similarity	NPC213052
0.8553	High Similarity	NPC474861
0.8544	High Similarity	NPC185103
0.8538	High Similarity	NPC105591
0.8537	High Similarity	NPC298847
0.8535	High Similarity	NPC205918
0.8533	High Similarity	NPC126739
0.8533	High Similarity	NPC197666
0.8521	High Similarity	NPC197357
0.8521	High Similarity	NPC85316
0.8516	High Similarity	NPC119767
0.8509	High Similarity	NPC472055
0.85	High Similarity	NPC177742
0.8497	Intermediate Similarity	NPC100242
0.8494	Intermediate Similarity	NPC315619
0.8491	Intermediate Similarity	NPC474501
0.8488	Intermediate Similarity	NPC205721
0.848	Intermediate Similarity	NPC241847
0.8471	Intermediate Similarity	NPC315520
0.8462	Intermediate Similarity	NPC84494
0.8462	Intermediate Similarity	NPC245059
0.8462	Intermediate Similarity	NPC72783
0.8462	Intermediate Similarity	NPC212290
0.8456	Intermediate Similarity	NPC142027
0.8456	Intermediate Similarity	NPC27407
0.8452	Intermediate Similarity	NPC324220
0.8452	Intermediate Similarity	NPC312630
0.8452	Intermediate Similarity	NPC147250
0.8447	Intermediate Similarity	NPC470339
0.8443	Intermediate Similarity	NPC98776
0.8442	Intermediate Similarity	NPC42540
0.8442	Intermediate Similarity	NPC151607
0.8438	Intermediate Similarity	NPC471787
0.8434	Intermediate Similarity	NPC470580
0.8434	Intermediate Similarity	NPC241874
0.8434	Intermediate Similarity	NPC52598
0.8431	Intermediate Similarity	NPC474300
0.8428	Intermediate Similarity	NPC472128
0.8428	Intermediate Similarity	NPC472127
0.8424	Intermediate Similarity	NPC107009
0.8424	Intermediate Similarity	NPC249977
0.8421	Intermediate Similarity	NPC168471
0.8421	Intermediate Similarity	NPC224557
0.8421	Intermediate Similarity	NPC292706
0.8421	Intermediate Similarity	NPC315578
0.8415	Intermediate Similarity	NPC7752
0.8412	Intermediate Similarity	NPC315221
0.8412	Intermediate Similarity	NPC164047
0.8412	Intermediate Similarity	NPC470453
0.8412	Intermediate Similarity	NPC470448
0.8412	Intermediate Similarity	NPC470452
0.8408	Intermediate Similarity	NPC120171
0.8408	Intermediate Similarity	NPC478219
0.8402	Intermediate Similarity	NPC469418
0.8397	Intermediate Similarity	NPC81835
0.8395	Intermediate Similarity	NPC470358
0.8393	Intermediate Similarity	NPC146803
0.8393	Intermediate Similarity	NPC307754
0.8393	Intermediate Similarity	NPC19056
0.8393	Intermediate Similarity	NPC470583
0.8393	Intermediate Similarity	NPC223735
0.8393	Intermediate Similarity	NPC70862
0.8385	Intermediate Similarity	NPC478226
0.8383	Intermediate Similarity	NPC270027
0.8377	Intermediate Similarity	NPC471731
0.8377	Intermediate Similarity	NPC476473
0.8377	Intermediate Similarity	NPC21873
0.8377	Intermediate Similarity	NPC159721
0.8375	Intermediate Similarity	NPC69043
0.8375	Intermediate Similarity	NPC478230
0.8375	Intermediate Similarity	NPC66029
0.8373	Intermediate Similarity	NPC191653
0.8373	Intermediate Similarity	NPC473202
0.8372	Intermediate Similarity	NPC87583
0.8366	Intermediate Similarity	NPC130485
0.8364	Intermediate Similarity	NPC469396
0.8364	Intermediate Similarity	NPC149002
0.8364	Intermediate Similarity	NPC469458
0.8364	Intermediate Similarity	NPC88176
0.8363	Intermediate Similarity	NPC313452
0.8355	Intermediate Similarity	NPC26924
0.8355	Intermediate Similarity	NPC295339
0.8354	Intermediate Similarity	NPC205766
0.8352	Intermediate Similarity	NPC42286
0.8344	Intermediate Similarity	NPC290695
0.8344	Intermediate Similarity	NPC261292

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 NPC82190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	812
0.2-0.3	1522
0.3-0.4	2588
0.4-0.5	2179
0.5-0.6	1193
0.6-0.7	419
0.7-0.8	137
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD8312	Approved
0.8675	High Similarity	NPD8313	Approved
0.8538	High Similarity	NPD7879	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD8150	Discontinued
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD6534	Approved
0.8125	Intermediate Similarity	NPD6535	Approved
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8122	Intermediate Similarity	NPD8320	Phase 1
0.8122	Intermediate Similarity	NPD8319	Approved
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.8072	Intermediate Similarity	NPD6232	Discontinued
0.8068	Intermediate Similarity	NPD6213	Phase 3
0.8068	Intermediate Similarity	NPD6212	Phase 3
0.8068	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD7435	Discontinued
0.8063	Intermediate Similarity	NPD3226	Approved
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD6780	Approved
0.8	Intermediate Similarity	NPD6777	Approved
0.8	Intermediate Similarity	NPD6779	Approved
0.8	Intermediate Similarity	NPD6776	Approved
0.8	Intermediate Similarity	NPD6778	Approved
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD6782	Approved
0.8	Intermediate Similarity	NPD6781	Approved
0.7989	Intermediate Similarity	NPD7700	Phase 2
0.7989	Intermediate Similarity	NPD7699	Phase 2
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7941	Intermediate Similarity	NPD7054	Approved
0.7939	Intermediate Similarity	NPD7075	Discontinued
0.7895	Intermediate Similarity	NPD7472	Approved
0.7871	Intermediate Similarity	NPD5404	Approved
0.7871	Intermediate Similarity	NPD5406	Approved
0.7871	Intermediate Similarity	NPD5408	Approved
0.7871	Intermediate Similarity	NPD5405	Approved
0.7866	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7390	Discontinued
0.7861	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6797	Phase 2
0.784	Intermediate Similarity	NPD7458	Discontinued
0.784	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7874	Approved
0.7807	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7772	Intermediate Similarity	NPD7698	Approved
0.7772	Intermediate Similarity	NPD7696	Phase 3
0.7772	Intermediate Similarity	NPD7697	Approved
0.7765	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6166	Phase 2
0.7765	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1201	Approved
0.7754	Intermediate Similarity	NPD8151	Discontinued
0.7744	Intermediate Similarity	NPD7411	Suspended
0.773	Intermediate Similarity	NPD7870	Phase 2
0.773	Intermediate Similarity	NPD7871	Phase 2
0.7717	Intermediate Similarity	NPD6823	Phase 2
0.7707	Intermediate Similarity	NPD7266	Discontinued
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7701	Intermediate Similarity	NPD7701	Phase 2
0.7697	Intermediate Similarity	NPD6801	Discontinued
0.7697	Intermediate Similarity	NPD1934	Approved
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7672	Intermediate Similarity	NPD7801	Approved
0.7672	Intermediate Similarity	NPD7783	Phase 2
0.7672	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1470	Approved
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD8455	Phase 2
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5402	Approved
0.759	Intermediate Similarity	NPD37	Approved
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.756	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7799	Discontinued
0.747	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5494	Approved
0.7411	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5401	Approved
0.7375	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD3300	Phase 2
0.7353	Intermediate Similarity	NPD7768	Phase 2
0.7346	Intermediate Similarity	NPD8166	Discontinued
0.7346	Intermediate Similarity	NPD7003	Approved
0.7345	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7337	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7317	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6799	Approved
0.731	Intermediate Similarity	NPD3749	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD7240	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD6674	Discontinued
0.7282	Intermediate Similarity	NPD7930	Approved
0.7273	Intermediate Similarity	NPD7177	Discontinued
0.7273	Intermediate Similarity	NPD2798	Approved
0.725	Intermediate Similarity	NPD2799	Discontinued
0.725	Intermediate Similarity	NPD1510	Phase 2
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD5710	Approved
0.7239	Intermediate Similarity	NPD3750	Approved
0.7239	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1465	Phase 2
0.7233	Intermediate Similarity	NPD1607	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7212	Intermediate Similarity	NPD1511	Approved
0.7205	Intermediate Similarity	NPD2438	Suspended
0.7205	Intermediate Similarity	NPD1551	Phase 2
0.72	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5125	Phase 3
0.7152	Intermediate Similarity	NPD5126	Approved
0.7151	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1512	Approved
0.7107	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD1240	Approved
0.7107	Intermediate Similarity	NPD943	Approved
0.7099	Intermediate Similarity	NPD6100	Approved
0.7099	Intermediate Similarity	NPD2796	Approved
0.7099	Intermediate Similarity	NPD6099	Approved
0.709	Intermediate Similarity	NPD8285	Discontinued
0.7081	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8059	Phase 3
0.7048	Intermediate Similarity	NPD7236	Approved
0.7047	Intermediate Similarity	NPD7999	Approved
0.7044	Intermediate Similarity	NPD6663	Approved
0.7041	Intermediate Similarity	NPD7239	Suspended
0.7032	Intermediate Similarity	NPD1283	Approved
0.7027	Intermediate Similarity	NPD8361	Approved
0.7027	Intermediate Similarity	NPD8360	Approved
0.7025	Intermediate Similarity	NPD7008	Discontinued
0.702	Intermediate Similarity	NPD9545	Approved
0.7013	Intermediate Similarity	NPD1608	Approved
0.701	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8127	Discontinued
0.6987	Remote Similarity	NPD1164	Approved
0.6984	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3268	Approved
0.6981	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD36	Approved
0.6978	Remote Similarity	NPD4954	Approved
0.6978	Remote Similarity	NPD5028	Approved
0.6978	Remote Similarity	NPD4955	Approved
0.6978	Remote Similarity	NPD5026	Approved
0.6978	Remote Similarity	NPD5034	Approved
0.697	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6832	Phase 2
0.6957	Remote Similarity	NPD1933	Approved
0.6951	Remote Similarity	NPD5763	Approved
0.6951	Remote Similarity	NPD5762	Approved
0.6944	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8435	Approved
0.6933	Remote Similarity	NPD3748	Approved
0.6933	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5030	Phase 2
0.6923	Remote Similarity	NPD8368	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