NPASS Compound

Structure

CID283480 OpenBabel06191716092D 37 40 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 2.5981 1.5000 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 -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 1 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 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 13 28 2 0 0 0 0 13 35 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 20 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 18 36 1 0 0 0 0 19 14 1 6 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 22 32 2 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 34 1 6 0 0 0 25 37 1 6 0 0 0 26 36 1 6 0 0 0 27 35 1 1 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.17
Volume:	502.86
LogP:	4.25
LogD:	2.261
LogS:	-4.23
# Rotatable Bonds:	6
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.199
Synthetic Accessibility Score:	4.415
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
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:	-5.782
MDCK Permeability:	2.0109178876737133e-05
Pgp-inhibitor:	0.157
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.655
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.54

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	96.22794342041016%
Volume Distribution (VD):	0.428
Pgp-substrate:	8.871042251586914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.587
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	1.267
Half-life (T1/2):	0.646

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.437
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.929
Carcinogencity:	0.077
Eye Corrosion:	0.008
Eye Irritation:	0.668
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC283480

Natural Product ID:	NPC283480
*Common Name:**	Alvaradoin H
IUPAC Name:	[(2S,3R,4R,5S,6S)-2-acetyloxy-6-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl] 3-methylbut-2-enoate
Synonyms:	Alvaradoin H
Standard InCHIKey:	NVWRUTJMHZBGQX-VJXMHWMPSA-N
Standard InCHI:	InChI=1S/C27H28O10/c1-11(2)8-18(31)36-26-23(33)25(37-27(24(26)34)35-13(4)28)19-14-6-5-7-16(29)20(14)22(32)21-15(19)9-12(3)10-17(21)30/h5-10,19,23-27,29-30,33-34H,1-4H3/t19-,23-,24+,25-,26+,27+/m0/s1
SMILES:	CC(=CC(=O)O[C@H]1[C@@H](O)[C@H](OC(=O)C)O[C@H]([C@@H]1O)[C@H]1c2cccc(c2C(=O)c2c1cc(C)cc2O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559908
PubChem CID:	16736265
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
ED50	2
Others	4

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	1070.0	nM	PMID[453418]
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	47.0	%	PMID[453419]
NPT91	Cell Line	KB	Homo sapiens	GI	=	43.0	%	PMID[453419]
NPT91	Cell Line	KB	Homo sapiens	GI	=	1.0	%	PMID[453419]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.29	uM	PMID[453419]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.29	uM	PMID[453419]
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	10.0	%	PMID[453419]

☑ 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 NPC283480 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	339
0.1-0.2	1276
0.2-0.3	2747
0.3-0.4	5805
0.4-0.5	10162
0.5-0.6	7533
0.6-0.7	6690
0.7-0.8	7408
0.8-0.85	587
0.85-0.9	116
0.9-0.95	22
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148323
0.9932	High Similarity	NPC82190
0.9932	High Similarity	NPC192219
0.9932	High Similarity	NPC174599
0.9865	High Similarity	NPC205172
0.9865	High Similarity	NPC209393
0.98	High Similarity	NPC208651
0.98	High Similarity	NPC206641
0.9673	High Similarity	NPC187934
0.9673	High Similarity	NPC97637
0.9667	High Similarity	NPC3449
0.9605	High Similarity	NPC53139
0.9324	High Similarity	NPC170055
0.9257	High Similarity	NPC218866
0.9257	High Similarity	NPC84568
0.9257	High Similarity	NPC48130
0.9257	High Similarity	NPC300684
0.9177	High Similarity	NPC478020
0.9177	High Similarity	NPC478022
0.9177	High Similarity	NPC178281
0.915	High Similarity	NPC474534
0.915	High Similarity	NPC474533
0.9133	High Similarity	NPC285122
0.9068	High Similarity	NPC298778
0.9051	High Similarity	NPC101116
0.9051	High Similarity	NPC278329
0.9051	High Similarity	NPC146837
0.9051	High Similarity	NPC212099
0.9051	High Similarity	NPC216752
0.9018	High Similarity	NPC474345
0.9012	High Similarity	NPC183441
0.8968	High Similarity	NPC474621
0.8968	High Similarity	NPC474622
0.8951	High Similarity	NPC478021
0.8902	High Similarity	NPC68381
0.8902	High Similarity	NPC470667
0.8896	High Similarity	NPC294501
0.8861	High Similarity	NPC314795
0.8848	High Similarity	NPC176246
0.8841	High Similarity	NPC472054
0.8841	High Similarity	NPC199357
0.8841	High Similarity	NPC85368
0.8841	High Similarity	NPC203751
0.882	High Similarity	NPC478026
0.8805	High Similarity	NPC328093
0.8802	High Similarity	NPC475161
0.8802	High Similarity	NPC477860
0.8797	High Similarity	NPC257309
0.8788	High Similarity	NPC186800
0.8782	High Similarity	NPC257847
0.878	High Similarity	NPC271385
0.878	High Similarity	NPC5029
0.878	High Similarity	NPC76128
0.878	High Similarity	NPC111536
0.878	High Similarity	NPC30432
0.8773	High Similarity	NPC259905
0.8765	High Similarity	NPC469419
0.8765	High Similarity	NPC178851
0.875	High Similarity	NPC473631
0.875	High Similarity	NPC293227
0.875	High Similarity	NPC475662
0.875	High Similarity	NPC473717
0.8735	High Similarity	NPC475246
0.8735	High Similarity	NPC102053
0.8735	High Similarity	NPC76112
0.8735	High Similarity	NPC289876
0.8735	High Similarity	NPC66820
0.8735	High Similarity	NPC92403
0.8735	High Similarity	NPC170018
0.8727	High Similarity	NPC65118
0.8712	High Similarity	NPC63470
0.871	High Similarity	NPC247219
0.8704	High Similarity	NPC99216
0.8704	High Similarity	NPC329647
0.8704	High Similarity	NPC470735
0.8688	High Similarity	NPC130489
0.8688	High Similarity	NPC208676
0.8679	High Similarity	NPC29552
0.8675	High Similarity	NPC3718
0.8675	High Similarity	NPC199533
0.8675	High Similarity	NPC470454
0.8675	High Similarity	NPC63105
0.8671	High Similarity	NPC472835
0.8659	High Similarity	NPC222455
0.8659	High Similarity	NPC175477
0.8659	High Similarity	NPC246274
0.8654	High Similarity	NPC475407
0.8647	High Similarity	NPC475352
0.8647	High Similarity	NPC473686
0.8647	High Similarity	NPC221140
0.8647	High Similarity	NPC475220
0.8647	High Similarity	NPC229817
0.8645	High Similarity	NPC94781
0.8642	High Similarity	NPC17432
0.8636	High Similarity	NPC120536
0.8634	High Similarity	NPC477627
0.8631	High Similarity	NPC114257
0.8631	High Similarity	NPC299149
0.8631	High Similarity	NPC58538
0.8631	High Similarity	NPC153578
0.8631	High Similarity	NPC277710
0.8627	High Similarity	NPC103910
0.8623	High Similarity	NPC475233
0.8623	High Similarity	NPC46958
0.8616	High Similarity	NPC478027
0.8614	High Similarity	NPC213052
0.8608	High Similarity	NPC182921
0.8608	High Similarity	NPC218870
0.8608	High Similarity	NPC474824
0.8608	High Similarity	NPC470408
0.8608	High Similarity	NPC185103
0.8598	High Similarity	NPC298847
0.8596	High Similarity	NPC105591
0.859	High Similarity	NPC44378
0.859	High Similarity	NPC280753
0.8581	High Similarity	NPC471734
0.858	High Similarity	NPC197357
0.858	High Similarity	NPC85316
0.8562	High Similarity	NPC177742
0.8562	High Similarity	NPC100242
0.8554	High Similarity	NPC315619
0.8553	High Similarity	NPC266469
0.8547	High Similarity	NPC205721
0.8538	High Similarity	NPC241847
0.8521	High Similarity	NPC212290
0.8521	High Similarity	NPC72783
0.8521	High Similarity	NPC84494
0.8521	High Similarity	NPC245059
0.8516	High Similarity	NPC471735
0.8503	High Similarity	NPC98776
0.85	High Similarity	NPC474861
0.8494	Intermediate Similarity	NPC470580
0.8494	Intermediate Similarity	NPC52598
0.8491	Intermediate Similarity	NPC472128
0.8491	Intermediate Similarity	NPC472127
0.8485	Intermediate Similarity	NPC249977
0.8481	Intermediate Similarity	NPC205918
0.848	Intermediate Similarity	NPC224557
0.848	Intermediate Similarity	NPC292706
0.8477	Intermediate Similarity	NPC126739
0.8477	Intermediate Similarity	NPC197666
0.8476	Intermediate Similarity	NPC7752
0.8471	Intermediate Similarity	NPC315221
0.8471	Intermediate Similarity	NPC164047
0.8471	Intermediate Similarity	NPC470453
0.8471	Intermediate Similarity	NPC470448
0.8471	Intermediate Similarity	NPC470452
0.8462	Intermediate Similarity	NPC119767
0.8462	Intermediate Similarity	NPC469418
0.8457	Intermediate Similarity	NPC470358
0.8457	Intermediate Similarity	NPC472055
0.8452	Intermediate Similarity	NPC146803
0.8452	Intermediate Similarity	NPC470583
0.8452	Intermediate Similarity	NPC19056
0.8452	Intermediate Similarity	NPC307754
0.8452	Intermediate Similarity	NPC70862
0.8452	Intermediate Similarity	NPC223735
0.8447	Intermediate Similarity	NPC478226
0.8443	Intermediate Similarity	NPC270027
0.8438	Intermediate Similarity	NPC474501
0.8434	Intermediate Similarity	NPC191653
0.8434	Intermediate Similarity	NPC473202
0.843	Intermediate Similarity	NPC87583
0.8424	Intermediate Similarity	NPC469396
0.8424	Intermediate Similarity	NPC469458
0.8424	Intermediate Similarity	NPC88176
0.8424	Intermediate Similarity	NPC149002
0.8421	Intermediate Similarity	NPC313452
0.8418	Intermediate Similarity	NPC315520
0.8409	Intermediate Similarity	NPC42286
0.8405	Intermediate Similarity	NPC69868
0.8402	Intermediate Similarity	NPC198893
0.8402	Intermediate Similarity	NPC314489
0.8402	Intermediate Similarity	NPC324220
0.8402	Intermediate Similarity	NPC312630
0.8402	Intermediate Similarity	NPC232818
0.84	Intermediate Similarity	NPC27407
0.84	Intermediate Similarity	NPC142027
0.8397	Intermediate Similarity	NPC470330
0.8397	Intermediate Similarity	NPC147250
0.8395	Intermediate Similarity	NPC470339
0.8395	Intermediate Similarity	NPC308265
0.8391	Intermediate Similarity	NPC314672
0.8387	Intermediate Similarity	NPC151607
0.8387	Intermediate Similarity	NPC42540
0.8385	Intermediate Similarity	NPC471787
0.8385	Intermediate Similarity	NPC127406
0.8383	Intermediate Similarity	NPC241874
0.8383	Intermediate Similarity	NPC76047
0.8377	Intermediate Similarity	NPC474300
0.8375	Intermediate Similarity	NPC279281
0.8375	Intermediate Similarity	NPC299761
0.8375	Intermediate Similarity	NPC230439
0.8375	Intermediate Similarity	NPC92153
0.8373	Intermediate Similarity	NPC107009
0.8366	Intermediate Similarity	NPC315578
0.8366	Intermediate Similarity	NPC168471
0.8354	Intermediate Similarity	NPC267469
0.8354	Intermediate Similarity	NPC259834
0.8354	Intermediate Similarity	NPC116292

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 NPC283480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	818
0.2-0.3	1532
0.3-0.4	2609
0.4-0.5	2168
0.5-0.6	1182
0.6-0.7	405
0.7-0.8	129
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8735	High Similarity	NPD8313	Approved
0.8735	High Similarity	NPD8312	Approved
0.8596	High Similarity	NPD7879	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD8150	Discontinued
0.8221	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6534	Approved
0.8182	Intermediate Similarity	NPD6535	Approved
0.8177	Intermediate Similarity	NPD8320	Phase 1
0.8177	Intermediate Similarity	NPD8319	Approved
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD6213	Phase 3
0.8125	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6212	Phase 3
0.8122	Intermediate Similarity	NPD7435	Discontinued
0.8107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7473	Discontinued
0.8075	Intermediate Similarity	NPD4380	Phase 2
0.8059	Intermediate Similarity	NPD7074	Phase 3
0.8057	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6778	Approved
0.8056	Intermediate Similarity	NPD6780	Approved
0.8056	Intermediate Similarity	NPD6776	Approved
0.8056	Intermediate Similarity	NPD6782	Approved
0.8056	Intermediate Similarity	NPD6779	Approved
0.8056	Intermediate Similarity	NPD6781	Approved
0.8056	Intermediate Similarity	NPD6777	Approved
0.8045	Intermediate Similarity	NPD7699	Phase 2
0.8045	Intermediate Similarity	NPD7700	Phase 2
0.8024	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD7054	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7953	Intermediate Similarity	NPD7472	Approved
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6797	Phase 2
0.7901	Intermediate Similarity	NPD7458	Discontinued
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD7075	Discontinued
0.7861	Intermediate Similarity	NPD7874	Approved
0.7861	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7251	Discontinued
0.7836	Intermediate Similarity	NPD3818	Discontinued
0.7826	Intermediate Similarity	NPD7696	Phase 3
0.7826	Intermediate Similarity	NPD7698	Approved
0.7826	Intermediate Similarity	NPD7697	Approved
0.7821	Intermediate Similarity	NPD5408	Approved
0.7821	Intermediate Similarity	NPD5404	Approved
0.7821	Intermediate Similarity	NPD5405	Approved
0.7821	Intermediate Similarity	NPD5406	Approved
0.7818	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7808	Phase 3
0.7812	Intermediate Similarity	NPD7390	Discontinued
0.7807	Intermediate Similarity	NPD8151	Discontinued
0.7791	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7870	Phase 2
0.7784	Intermediate Similarity	NPD7871	Phase 2
0.7772	Intermediate Similarity	NPD6823	Phase 2
0.7771	Intermediate Similarity	NPD7266	Discontinued
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7701	Phase 2
0.7733	Intermediate Similarity	NPD7228	Approved
0.7725	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7783	Phase 2
0.7725	Intermediate Similarity	NPD7801	Approved
0.7719	Intermediate Similarity	NPD6166	Phase 2
0.7719	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1201	Approved
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7654	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD1934	Approved
0.7651	Intermediate Similarity	NPD6801	Discontinued
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4965	Approved
0.7616	Intermediate Similarity	NPD1470	Approved
0.756	Intermediate Similarity	NPD5402	Approved
0.7557	Intermediate Similarity	NPD7685	Pre-registration
0.7553	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7799	Discontinued
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD6190	Approved
0.7462	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3817	Phase 2
0.7455	Intermediate Similarity	NPD5403	Approved
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7439	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD5494	Approved
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7240	Approved
0.7346	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7930	Approved
0.7329	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3300	Phase 2
0.731	Intermediate Similarity	NPD7768	Phase 2
0.7303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8166	Discontinued
0.7301	Intermediate Similarity	NPD7003	Approved
0.7294	Intermediate Similarity	NPD2801	Approved
0.7284	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD3749	Approved
0.7261	Intermediate Similarity	NPD3764	Approved
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7246	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7177	Discontinued
0.7226	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD5125	Phase 3
0.7219	Intermediate Similarity	NPD5126	Approved
0.7205	Intermediate Similarity	NPD1510	Phase 2
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.7195	Intermediate Similarity	NPD3750	Approved
0.7193	Intermediate Similarity	NPD1465	Phase 2
0.7188	Intermediate Similarity	NPD1607	Approved
0.7186	Intermediate Similarity	NPD6273	Approved
0.7169	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD2438	Suspended
0.716	Intermediate Similarity	NPD1551	Phase 2
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3882	Suspended
0.7108	Intermediate Similarity	NPD8059	Phase 3
0.7108	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7098	Intermediate Similarity	NPD7999	Approved
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1512	Approved
0.7063	Intermediate Similarity	NPD943	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1240	Approved
0.7062	Intermediate Similarity	NPD7584	Approved
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD2796	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7053	Intermediate Similarity	NPD8285	Discontinued
0.7019	Intermediate Similarity	NPD1933	Approved
0.7019	Intermediate Similarity	NPD230	Phase 1
0.7006	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8361	Approved
0.6989	Remote Similarity	NPD8360	Approved
0.6987	Remote Similarity	NPD1283	Approved
0.6981	Remote Similarity	NPD7008	Discontinued
0.6978	Remote Similarity	NPD8368	Discontinued
0.6974	Remote Similarity	NPD9545	Approved
0.6968	Remote Similarity	NPD1608	Approved
0.6963	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5736	Approved
0.6957	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD9493	Approved
0.6949	Remote Similarity	NPD8127	Discontinued
0.6947	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1164	Approved
0.694	Remote Similarity	NPD5034	Approved
0.694	Remote Similarity	NPD4954	Approved
0.694	Remote Similarity	NPD5028	Approved
0.694	Remote Similarity	NPD36	Approved
0.694	Remote Similarity	NPD5026	Approved
0.694	Remote Similarity	NPD4955	Approved
0.6937	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.6907	Remote Similarity	NPD7680	Approved
0.6901	Remote Similarity	NPD1653	Approved
0.6899	Remote Similarity	NPD6007	Clinical (unspecified phase)

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