NPASS Compound

Structure

NPC205172 OpenBabel07101719512D 31 34 0 0 1 0 0 0 0 0999 V2000 -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 -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 -3.4641 -2.0000 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 -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 -1.7321 0.0000 0.0000 C 0 0 2 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 -0.0000 -2.0000 0.0000 C 0 0 2 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 -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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -5.1962 0.0000 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 -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 -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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 9 23 2 0 0 0 0 9 30 1 0 0 0 0 10 15 2 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 10 1 1 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 17 26 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 22 1 0 0 0 0 20 29 1 6 0 0 0 21 31 1 1 0 0 0 22 30 1 6 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.13
Volume:	412.863
LogP:	3.123
LogD:	1.45
LogS:	-2.777
# Rotatable Bonds:	3
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	4.116
Fsp3:	0.318
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:	-6.291
MDCK Permeability:	6.078178103052778e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.533
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	94.869873046875%
Volume Distribution (VD):	0.564
Pgp-substrate:	7.1392717361450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.598
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.654
CYP2D6-inhibitor:	0.454
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	1.168
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.766
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.555
Skin Sensitization:	0.913
Carcinogencity:	0.23
Eye Corrosion:	0.003
Eye Irritation:	0.718
Respiratory Toxicity:	0.146

Download Data

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

Natural Product: NPC205172

Natural Product ID:	NPC205172
*Common Name:**	Alvaradoin F
IUPAC Name:	[(2R,3R,4R,5R,6R)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,4,5-trihydroxyoxan-2-yl] acetate
Synonyms:	Alvaradoin F
Standard InCHIKey:	ANCSMTDJGPZSRP-MGOVIWOVSA-N
Standard InCHI:	InChI=1S/C22H22O9/c1-8-6-11-14(21-19(28)18(27)20(29)22(31-21)30-9(2)23)10-4-3-5-12(24)15(10)17(26)16(11)13(25)7-8/h3-7,14,18-22,24-25,27-29H,1-2H3/t14-,18-,19-,20-,21-,22+/m1/s1
SMILES:	CC(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)[C@@H]1c2cccc(c2C(=O)c2c1cc(C)cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229574
PubChem CID:	44424597
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	3
Others	7

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	65.0	nM	PMID[564933]
NPT168	Cell Line	P388	Mus musculus	Activity	=	115.0	%	PMID[564933]
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	59.0	%	PMID[564934]
NPT91	Cell Line	KB	Homo sapiens	GI	=	32.0	%	PMID[564934]
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	3.0	%	PMID[564934]
NPT1851	Cell Line	Col2	Homo sapiens	GI	=	21.0	%	PMID[564934]
NPT91	Cell Line	KB	Homo sapiens	GI	=	2.0	%	PMID[564934]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	0.23	uM	PMID[564934]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.23	uM	PMID[564934]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.12	uM	PMID[564934]
NPT1851	Cell Line	Col2	Homo sapiens	GI	=	1.0	%	PMID[564934]

☑ 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 NPC205172 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	332
0.1-0.2	1243
0.2-0.3	2730
0.3-0.4	5920
0.4-0.5	10448
0.5-0.6	7506
0.6-0.7	7279
0.7-0.8	6727
0.8-0.85	397
0.85-0.9	90
0.9-0.95	13
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209393
0.9865	High Similarity	NPC283480
0.9865	High Similarity	NPC148323
0.9797	High Similarity	NPC192219
0.9797	High Similarity	NPC3449
0.9797	High Similarity	NPC174599
0.9797	High Similarity	NPC82190
0.9667	High Similarity	NPC208651
0.9667	High Similarity	NPC206641
0.9542	High Similarity	NPC187934
0.9542	High Similarity	NPC97637
0.9474	High Similarity	NPC53139
0.9452	High Similarity	NPC170055
0.9384	High Similarity	NPC218866
0.9384	High Similarity	NPC84568
0.9384	High Similarity	NPC300684
0.9384	High Similarity	NPC48130
0.9257	High Similarity	NPC285122
0.9051	High Similarity	NPC478020
0.9051	High Similarity	NPC478022
0.9051	High Similarity	NPC178281
0.902	High Similarity	NPC474534
0.902	High Similarity	NPC474533
0.8974	High Similarity	NPC314795
0.8944	High Similarity	NPC298778
0.8924	High Similarity	NPC212099
0.8924	High Similarity	NPC216752
0.8924	High Similarity	NPC278329
0.8924	High Similarity	NPC146837
0.8924	High Similarity	NPC101116
0.8896	High Similarity	NPC474345
0.8889	High Similarity	NPC183441
0.8839	High Similarity	NPC474621
0.8839	High Similarity	NPC474622
0.8827	High Similarity	NPC478021
0.878	High Similarity	NPC470667
0.878	High Similarity	NPC68381
0.8773	High Similarity	NPC294501
0.8766	High Similarity	NPC475407
0.8758	High Similarity	NPC94781
0.875	High Similarity	NPC120536
0.8727	High Similarity	NPC176246
0.872	High Similarity	NPC85368
0.872	High Similarity	NPC199357
0.872	High Similarity	NPC203751
0.872	High Similarity	NPC472054
0.8718	High Similarity	NPC182921
0.8718	High Similarity	NPC474824
0.8718	High Similarity	NPC218870
0.8718	High Similarity	NPC470408
0.8701	High Similarity	NPC44378
0.8701	High Similarity	NPC280753
0.8696	High Similarity	NPC478026
0.8683	High Similarity	NPC477860
0.8683	High Similarity	NPC475161
0.8679	High Similarity	NPC328093
0.8675	High Similarity	NPC100242
0.8671	High Similarity	NPC257309
0.8667	High Similarity	NPC186800
0.8662	High Similarity	NPC266469
0.8659	High Similarity	NPC271385
0.8659	High Similarity	NPC5029
0.8659	High Similarity	NPC30432
0.8659	High Similarity	NPC76128
0.8659	High Similarity	NPC111536
0.8654	High Similarity	NPC257847
0.865	High Similarity	NPC259905
0.8642	High Similarity	NPC469419
0.8642	High Similarity	NPC178851
0.8631	High Similarity	NPC473631
0.8631	High Similarity	NPC475662
0.8631	High Similarity	NPC293227
0.8631	High Similarity	NPC473717
0.8614	High Similarity	NPC102053
0.8614	High Similarity	NPC76112
0.8614	High Similarity	NPC66820
0.8614	High Similarity	NPC170018
0.8614	High Similarity	NPC92403
0.8614	High Similarity	NPC475246
0.8614	High Similarity	NPC289876
0.8608	High Similarity	NPC474861
0.8606	High Similarity	NPC65118
0.859	High Similarity	NPC205918
0.8589	High Similarity	NPC63470
0.8581	High Similarity	NPC247219
0.858	High Similarity	NPC99216
0.858	High Similarity	NPC329647
0.858	High Similarity	NPC470735
0.8562	High Similarity	NPC130489
0.8562	High Similarity	NPC208676
0.8554	High Similarity	NPC199533
0.8554	High Similarity	NPC63105
0.8554	High Similarity	NPC3718
0.8554	High Similarity	NPC470454
0.8553	High Similarity	NPC29552
0.8544	High Similarity	NPC472835
0.8544	High Similarity	NPC474501
0.8537	High Similarity	NPC246274
0.8537	High Similarity	NPC222455
0.8537	High Similarity	NPC175477
0.8529	High Similarity	NPC475220
0.8529	High Similarity	NPC473686
0.8529	High Similarity	NPC229817
0.8529	High Similarity	NPC475352
0.8529	High Similarity	NPC221140
0.8526	High Similarity	NPC315520
0.8519	High Similarity	NPC17432
0.8512	High Similarity	NPC114257
0.8512	High Similarity	NPC299149
0.8512	High Similarity	NPC277710
0.8512	High Similarity	NPC58538
0.8512	High Similarity	NPC153578
0.8509	High Similarity	NPC477627
0.8506	High Similarity	NPC470330
0.8503	High Similarity	NPC46958
0.8503	High Similarity	NPC475233
0.8497	Intermediate Similarity	NPC103910
0.8494	Intermediate Similarity	NPC213052
0.8491	Intermediate Similarity	NPC478027
0.8481	Intermediate Similarity	NPC185103
0.848	Intermediate Similarity	NPC105591
0.8477	Intermediate Similarity	NPC315578
0.8476	Intermediate Similarity	NPC298847
0.8462	Intermediate Similarity	NPC120171
0.8462	Intermediate Similarity	NPC85316
0.8462	Intermediate Similarity	NPC197357
0.8452	Intermediate Similarity	NPC471734
0.8438	Intermediate Similarity	NPC177742
0.8434	Intermediate Similarity	NPC315619
0.843	Intermediate Similarity	NPC205721
0.8421	Intermediate Similarity	NPC241847
0.8411	Intermediate Similarity	NPC26924
0.8402	Intermediate Similarity	NPC245059
0.8402	Intermediate Similarity	NPC212290
0.8402	Intermediate Similarity	NPC84494
0.8402	Intermediate Similarity	NPC72783
0.8387	Intermediate Similarity	NPC471735
0.8383	Intermediate Similarity	NPC98776
0.8373	Intermediate Similarity	NPC52598
0.8373	Intermediate Similarity	NPC470580
0.8365	Intermediate Similarity	NPC472127
0.8365	Intermediate Similarity	NPC472128
0.8364	Intermediate Similarity	NPC249977
0.8363	Intermediate Similarity	NPC292706
0.8363	Intermediate Similarity	NPC224557
0.8355	Intermediate Similarity	NPC3218
0.8354	Intermediate Similarity	NPC7752
0.8353	Intermediate Similarity	NPC470453
0.8353	Intermediate Similarity	NPC470452
0.8353	Intermediate Similarity	NPC470448
0.8353	Intermediate Similarity	NPC315221
0.8353	Intermediate Similarity	NPC164047
0.8344	Intermediate Similarity	NPC126739
0.8344	Intermediate Similarity	NPC197666
0.8343	Intermediate Similarity	NPC469418
0.8333	Intermediate Similarity	NPC119767
0.8333	Intermediate Similarity	NPC19056
0.8333	Intermediate Similarity	NPC470583
0.8333	Intermediate Similarity	NPC146803
0.8333	Intermediate Similarity	NPC307754
0.8333	Intermediate Similarity	NPC70862
0.8333	Intermediate Similarity	NPC223735
0.8333	Intermediate Similarity	NPC472055
0.8333	Intermediate Similarity	NPC470358
0.8323	Intermediate Similarity	NPC270027
0.8323	Intermediate Similarity	NPC478226
0.8314	Intermediate Similarity	NPC87583
0.8313	Intermediate Similarity	NPC191653
0.8313	Intermediate Similarity	NPC473202
0.8304	Intermediate Similarity	NPC313452
0.8303	Intermediate Similarity	NPC469396
0.8303	Intermediate Similarity	NPC149002
0.8303	Intermediate Similarity	NPC469458
0.8303	Intermediate Similarity	NPC88176
0.8295	Intermediate Similarity	NPC42286
0.8284	Intermediate Similarity	NPC314489
0.8284	Intermediate Similarity	NPC198893
0.8284	Intermediate Similarity	NPC324220
0.8284	Intermediate Similarity	NPC312630
0.8284	Intermediate Similarity	NPC232818
0.8282	Intermediate Similarity	NPC69868
0.8276	Intermediate Similarity	NPC314672
0.8272	Intermediate Similarity	NPC308265
0.8272	Intermediate Similarity	NPC470339
0.8269	Intermediate Similarity	NPC63918
0.8269	Intermediate Similarity	NPC147250
0.8269	Intermediate Similarity	NPC314437
0.8267	Intermediate Similarity	NPC142027
0.8267	Intermediate Similarity	NPC27407
0.8263	Intermediate Similarity	NPC241874
0.8263	Intermediate Similarity	NPC76047
0.8261	Intermediate Similarity	NPC127406
0.8261	Intermediate Similarity	NPC10945
0.8261	Intermediate Similarity	NPC471787
0.8258	Intermediate Similarity	NPC151607
0.8258	Intermediate Similarity	NPC42540
0.8258	Intermediate Similarity	NPC244691
0.8253	Intermediate Similarity	NPC471295
0.8253	Intermediate Similarity	NPC107009
0.825	Intermediate Similarity	NPC92153

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 NPC205172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	810
0.2-0.3	1521
0.3-0.4	2641
0.4-0.5	2242
0.5-0.6	1138
0.6-0.7	386
0.7-0.8	122
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD8313	Approved
0.8614	High Similarity	NPD8312	Approved
0.848	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD8150	Discontinued
0.8098	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6534	Approved
0.8068	Intermediate Similarity	NPD6535	Approved
0.8066	Intermediate Similarity	NPD8320	Phase 1
0.8066	Intermediate Similarity	NPD8319	Approved
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8011	Intermediate Similarity	NPD6212	Phase 3
0.8011	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7435	Discontinued
0.8011	Intermediate Similarity	NPD6213	Phase 3
0.7988	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7944	Intermediate Similarity	NPD6781	Approved
0.7944	Intermediate Similarity	NPD6782	Approved
0.7944	Intermediate Similarity	NPD6779	Approved
0.7944	Intermediate Similarity	NPD6776	Approved
0.7944	Intermediate Similarity	NPD6780	Approved
0.7944	Intermediate Similarity	NPD6778	Approved
0.7944	Intermediate Similarity	NPD6777	Approved
0.7943	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7074	Phase 3
0.7933	Intermediate Similarity	NPD7700	Phase 2
0.7933	Intermediate Similarity	NPD7699	Phase 2
0.7922	Intermediate Similarity	NPD5408	Approved
0.7922	Intermediate Similarity	NPD5405	Approved
0.7922	Intermediate Similarity	NPD5404	Approved
0.7922	Intermediate Similarity	NPD5406	Approved
0.7911	Intermediate Similarity	NPD7390	Discontinued
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7888	Intermediate Similarity	NPD3226	Approved
0.7882	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6959	Discontinued
0.7836	Intermediate Similarity	NPD7472	Approved
0.7808	Intermediate Similarity	NPD1201	Approved
0.7805	Intermediate Similarity	NPD7819	Suspended
0.7803	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7458	Discontinued
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7754	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7874	Approved
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3818	Discontinued
0.7718	Intermediate Similarity	NPD1470	Approved
0.7717	Intermediate Similarity	NPD7696	Phase 3
0.7717	Intermediate Similarity	NPD7697	Approved
0.7717	Intermediate Similarity	NPD7698	Approved
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD8151	Discontinued
0.7697	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7871	Phase 2
0.7676	Intermediate Similarity	NPD7870	Phase 2
0.7669	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6823	Phase 2
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7701	Phase 2
0.7643	Intermediate Similarity	NPD7266	Discontinued
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7619	Intermediate Similarity	NPD7783	Phase 2
0.7619	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7801	Approved
0.7616	Intermediate Similarity	NPD7228	Approved
0.7602	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8455	Phase 2
0.7576	Intermediate Similarity	NPD7411	Suspended
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2534	Approved
0.7531	Intermediate Similarity	NPD2533	Approved
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD1934	Approved
0.753	Intermediate Similarity	NPD6801	Discontinued
0.753	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD5402	Approved
0.7414	Intermediate Similarity	NPD7799	Discontinued
0.7407	Intermediate Similarity	NPD3300	Phase 2
0.7403	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2935	Discontinued
0.7346	Intermediate Similarity	NPD6190	Approved
0.7337	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD5403	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7317	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD5494	Approved
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7240	Approved
0.7231	Intermediate Similarity	NPD7930	Approved
0.7222	Intermediate Similarity	NPD6674	Discontinued
0.7212	Intermediate Similarity	NPD5401	Approved
0.7212	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7191	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8166	Discontinued
0.7178	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2801	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD943	Approved
0.7151	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3764	Approved
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7097	Intermediate Similarity	NPD2798	Approved
0.7089	Intermediate Similarity	NPD6663	Approved
0.7086	Intermediate Similarity	NPD5125	Phase 3
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7086	Intermediate Similarity	NPD5126	Approved
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7081	Intermediate Similarity	NPD2799	Discontinued
0.7076	Intermediate Similarity	NPD1465	Phase 2
0.7073	Intermediate Similarity	NPD3750	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7063	Intermediate Similarity	NPD1607	Approved
0.7051	Intermediate Similarity	NPD5736	Approved
0.7048	Intermediate Similarity	NPD1511	Approved
0.7037	Intermediate Similarity	NPD1551	Phase 2
0.7037	Intermediate Similarity	NPD2438	Suspended
0.7032	Intermediate Similarity	NPD1164	Approved
0.7025	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4955	Approved
0.7017	Intermediate Similarity	NPD4954	Approved
0.7017	Intermediate Similarity	NPD5034	Approved
0.7017	Intermediate Similarity	NPD36	Approved
0.7017	Intermediate Similarity	NPD5026	Approved
0.7017	Intermediate Similarity	NPD5028	Approved
0.701	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8059	Phase 3
0.6995	Remote Similarity	NPD7999	Approved
0.6994	Remote Similarity	NPD3882	Suspended
0.6987	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7033	Discontinued
0.6975	Remote Similarity	NPD651	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1512	Approved
0.6961	Remote Similarity	NPD5030	Phase 2
0.6959	Remote Similarity	NPD7584	Approved
0.6957	Remote Similarity	NPD5038	Approved
0.6957	Remote Similarity	NPD5037	Approved
0.6947	Remote Similarity	NPD8285	Discontinued
0.6937	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1240	Approved
0.6937	Remote Similarity	NPD4060	Phase 1
0.6933	Remote Similarity	NPD2796	Approved
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6100	Approved
0.6913	Remote Similarity	NPD5951	Approved
0.6902	Remote Similarity	NPD5036	Approved
0.6894	Remote Similarity	NPD230	Phase 1
0.6894	Remote Similarity	NPD1933	Approved
0.6889	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7236	Approved
0.6882	Remote Similarity	NPD8361	Approved
0.6882	Remote Similarity	NPD7239	Suspended
0.6882	Remote Similarity	NPD8360	Approved
0.6868	Remote Similarity	NPD8368	Discontinued
0.6867	Remote Similarity	NPD3400	Discontinued
0.6863	Remote Similarity	NPD3019	Approved
0.6859	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7008	Discontinued
0.6842	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1608	Approved
0.6836	Remote Similarity	NPD8127	Discontinued
0.6832	Remote Similarity	NPD2979	Phase 3
0.6821	Remote Similarity	NPD9493	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