NPASS Compound

Structure

CID318751 OpenBabel06191716142D 35 41 0 0 1 0 0 0 0 0999 V2000 0.7573 -0.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1828 -1.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4658 0.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9524 -2.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0619 -2.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6145 0.2398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3465 -0.8318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8908 -0.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1681 -2.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8776 -1.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 -0.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6640 -2.0845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8246 -0.4046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7707 -1.3850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3085 -1.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3621 0.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8770 -0.6758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5616 -0.8818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3617 -0.3127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6989 -1.3689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7446 -0.1871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8846 -1.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5139 -0.0140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3471 -1.5304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7053 0.2204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2944 -1.5352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6305 -0.5493 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3628 -0.7156 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9823 -0.5124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8321 -0.0694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6393 -1.6970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8408 0.8347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5810 1.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9735 0.3148 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 7 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 15 28 1 0 0 0 0 16 25 1 0 0 0 0 16 34 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 24 1 0 0 0 0 20 27 1 6 0 0 0 21 25 1 6 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 29 1 0 0 0 0 22 31 2 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 25 6 1 1 0 0 0 25 33 1 0 0 0 0 26 28 1 6 0 0 0 27 11 1 1 0 0 0 27 35 1 0 0 0 0 28 30 1 6 0 0 0 29 17 1 6 0 0 0 30 23 1 6 0 0 0 30 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.29
Volume:	500.946
LogP:	4.879
LogD:	3.935
LogS:	-4.857
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	5.809
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.325
MDCK Permeability:	2.8178463253425434e-05
Pgp-inhibitor:	0.565
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.349
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	85.66779327392578%
Volume Distribution (VD):	2.222
Pgp-substrate:	9.051237106323242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	10.939
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.693
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.606
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.246
Carcinogencity:	0.961
Eye Corrosion:	0.045
Eye Irritation:	0.023
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC318751

Natural Product ID:	NPC318751
*Common Name:**	Salvadione C
IUPAC Name:	n.a.
Synonyms:	Salvadione C
Standard InCHIKey:	FOQBZJXMAZZAIA-NQWLPLNFSA-N
Standard InCHI:	InChI=1S/C30H40O5/c1-7-18-13-19-21-25(6,33)16-34-30-23(32)29(21,17(2)3)22(31)26(14-18)12-9-20-24(4,5)10-8-11-27(20,35-30)15-28(19,26)30/h7,13,17,19-21,33H,1,8-12,14-16H2,2-6H3/t19-,20+,21+,25-,26+,27+,28+,29-,30+/m1/s1
SMILES:	CC(C)C12C3C4C=C(CC5(C1=O)C46CC7(CCCC(C7CC5)(C)C)OC6(C2=O)OCC3(C)O)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928366
PubChem CID:	56600678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO24632	Salvia hydrangea	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21967089]
NPO24632	Salvia hydrangea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30565934]
NPO24632	Salvia hydrangea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24632	Salvia hydrangea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90000.0	nM	PMID[533102]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1430.0	nM	PMID[533102]
NPT2	Others	Unspecified		Ratio IC50	=	86.6	n.a.	PMID[533102]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	4330.0	nM	PMID[533102]
NPT2	Others	Unspecified		Ratio IC50	=	43.2	n.a.	PMID[533102]

☑ 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 NPC318751 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	286
0.1-0.2	1707
0.2-0.3	5540
0.3-0.4	11453
0.4-0.5	11678
0.5-0.6	7148
0.6-0.7	3950
0.7-0.8	932
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8145	Intermediate Similarity	NPC188291
0.7984	Intermediate Similarity	NPC243014
0.7983	Intermediate Similarity	NPC152199
0.7983	Intermediate Similarity	NPC235539
0.7983	Intermediate Similarity	NPC134869
0.7969	Intermediate Similarity	NPC242486
0.7969	Intermediate Similarity	NPC15215
0.7953	Intermediate Similarity	NPC100390
0.7953	Intermediate Similarity	NPC254614
0.7937	Intermediate Similarity	NPC264192
0.7899	Intermediate Similarity	NPC474906
0.7899	Intermediate Similarity	NPC18547
0.7886	Intermediate Similarity	NPC275343
0.7851	Intermediate Similarity	NPC297179
0.7838	Intermediate Similarity	NPC272451
0.7833	Intermediate Similarity	NPC259306
0.7833	Intermediate Similarity	NPC328374
0.7833	Intermediate Similarity	NPC474046
0.7833	Intermediate Similarity	NPC96312
0.7833	Intermediate Similarity	NPC40632
0.7833	Intermediate Similarity	NPC470628
0.7833	Intermediate Similarity	NPC251236
0.7812	Intermediate Similarity	NPC6274
0.7812	Intermediate Similarity	NPC254146
0.7812	Intermediate Similarity	NPC33378
0.7797	Intermediate Similarity	NPC201992
0.7759	Intermediate Similarity	NPC144854
0.7759	Intermediate Similarity	NPC3316
0.775	Intermediate Similarity	NPC470919
0.775	Intermediate Similarity	NPC469877
0.775	Intermediate Similarity	NPC473798
0.7742	Intermediate Similarity	NPC235438
0.7742	Intermediate Similarity	NPC107966
0.7742	Intermediate Similarity	NPC249848
0.7742	Intermediate Similarity	NPC40775
0.7731	Intermediate Similarity	NPC205534
0.7731	Intermediate Similarity	NPC11252
0.7731	Intermediate Similarity	NPC289312
0.7731	Intermediate Similarity	NPC474516
0.7727	Intermediate Similarity	NPC293086
0.7724	Intermediate Similarity	NPC478051
0.7712	Intermediate Similarity	NPC470065
0.7712	Intermediate Similarity	NPC210005
0.7705	Intermediate Similarity	NPC286347
0.7705	Intermediate Similarity	NPC17772
0.7698	Intermediate Similarity	NPC285091
0.7692	Intermediate Similarity	NPC154608
0.7692	Intermediate Similarity	NPC192813
0.7692	Intermediate Similarity	NPC277017
0.7686	Intermediate Similarity	NPC474734
0.768	Intermediate Similarity	NPC235405
0.768	Intermediate Similarity	NPC30735
0.768	Intermediate Similarity	NPC281148
0.7672	Intermediate Similarity	NPC181357
0.7667	Intermediate Similarity	NPC51978
0.7667	Intermediate Similarity	NPC49451
0.7661	Intermediate Similarity	NPC75417
0.7642	Intermediate Similarity	NPC208381
0.7642	Intermediate Similarity	NPC157868
0.7642	Intermediate Similarity	NPC180550
0.7642	Intermediate Similarity	NPC114441
0.7642	Intermediate Similarity	NPC6377
0.7642	Intermediate Similarity	NPC469945
0.7642	Intermediate Similarity	NPC192791
0.7642	Intermediate Similarity	NPC473920
0.7642	Intermediate Similarity	NPC39211
0.7642	Intermediate Similarity	NPC35405
0.7642	Intermediate Similarity	NPC475171
0.7642	Intermediate Similarity	NPC11551
0.7642	Intermediate Similarity	NPC472949
0.7642	Intermediate Similarity	NPC309780
0.7642	Intermediate Similarity	NPC268958
0.7642	Intermediate Similarity	NPC473884
0.7642	Intermediate Similarity	NPC214484
0.7627	Intermediate Similarity	NPC141350
0.7623	Intermediate Similarity	NPC473590
0.7623	Intermediate Similarity	NPC224121
0.7619	Intermediate Similarity	NPC470477
0.7603	Intermediate Similarity	NPC247069
0.76	Intermediate Similarity	NPC162574
0.76	Intermediate Similarity	NPC471965
0.7583	Intermediate Similarity	NPC302146
0.7583	Intermediate Similarity	NPC193948
0.7583	Intermediate Similarity	NPC130427
0.7581	Intermediate Similarity	NPC109607
0.7581	Intermediate Similarity	NPC107338
0.7581	Intermediate Similarity	NPC472257
0.7581	Intermediate Similarity	NPC472076
0.7581	Intermediate Similarity	NPC294112
0.7581	Intermediate Similarity	NPC472075
0.7578	Intermediate Similarity	NPC473888
0.7563	Intermediate Similarity	NPC474567
0.7561	Intermediate Similarity	NPC109588
0.7561	Intermediate Similarity	NPC204552
0.7561	Intermediate Similarity	NPC188667
0.7561	Intermediate Similarity	NPC470776
0.7559	Intermediate Similarity	NPC469947
0.7559	Intermediate Similarity	NPC470218
0.7559	Intermediate Similarity	NPC181066
0.7544	Intermediate Similarity	NPC474802
0.7542	Intermediate Similarity	NPC272576
0.7542	Intermediate Similarity	NPC168883
0.7542	Intermediate Similarity	NPC258323
0.7541	Intermediate Similarity	NPC16081
0.7541	Intermediate Similarity	NPC173686
0.7541	Intermediate Similarity	NPC473126
0.7541	Intermediate Similarity	NPC179626
0.754	Intermediate Similarity	NPC262199
0.754	Intermediate Similarity	NPC472077
0.754	Intermediate Similarity	NPC471964
0.754	Intermediate Similarity	NPC471961
0.754	Intermediate Similarity	NPC18945
0.754	Intermediate Similarity	NPC105926
0.754	Intermediate Similarity	NPC91693
0.754	Intermediate Similarity	NPC202666
0.754	Intermediate Similarity	NPC478066
0.754	Intermediate Similarity	NPC472078
0.754	Intermediate Similarity	NPC227397
0.754	Intermediate Similarity	NPC14617
0.754	Intermediate Similarity	NPC265557
0.7538	Intermediate Similarity	NPC102316
0.7521	Intermediate Similarity	NPC178981
0.7521	Intermediate Similarity	NPC62696
0.7521	Intermediate Similarity	NPC293038
0.7521	Intermediate Similarity	NPC477266
0.7521	Intermediate Similarity	NPC474271
0.7521	Intermediate Similarity	NPC102352
0.752	Intermediate Similarity	NPC114484
0.752	Intermediate Similarity	NPC242840
0.752	Intermediate Similarity	NPC104372
0.752	Intermediate Similarity	NPC102822
0.752	Intermediate Similarity	NPC22956
0.752	Intermediate Similarity	NPC64715
0.752	Intermediate Similarity	NPC86222
0.752	Intermediate Similarity	NPC222580
0.752	Intermediate Similarity	NPC62725
0.752	Intermediate Similarity	NPC223301
0.752	Intermediate Similarity	NPC31838
0.752	Intermediate Similarity	NPC477046
0.752	Intermediate Similarity	NPC301449
0.752	Intermediate Similarity	NPC470779
0.752	Intermediate Similarity	NPC31193
0.752	Intermediate Similarity	NPC297263
0.752	Intermediate Similarity	NPC159309
0.752	Intermediate Similarity	NPC171544
0.752	Intermediate Similarity	NPC11242
0.75	Intermediate Similarity	NPC469488
0.75	Intermediate Similarity	NPC471243
0.75	Intermediate Similarity	NPC475775
0.75	Intermediate Similarity	NPC476529
0.75	Intermediate Similarity	NPC470777
0.75	Intermediate Similarity	NPC275583
0.75	Intermediate Similarity	NPC279143
0.748	Intermediate Similarity	NPC474654
0.748	Intermediate Similarity	NPC97908
0.748	Intermediate Similarity	NPC122033
0.748	Intermediate Similarity	NPC477116
0.748	Intermediate Similarity	NPC247315
0.748	Intermediate Similarity	NPC287343
0.748	Intermediate Similarity	NPC309433
0.748	Intermediate Similarity	NPC23046
0.748	Intermediate Similarity	NPC470922
0.748	Intermediate Similarity	NPC470854
0.748	Intermediate Similarity	NPC476729
0.748	Intermediate Similarity	NPC471963
0.748	Intermediate Similarity	NPC471962
0.748	Intermediate Similarity	NPC27999
0.7479	Intermediate Similarity	NPC300026
0.7479	Intermediate Similarity	NPC143706
0.7479	Intermediate Similarity	NPC153239
0.7479	Intermediate Similarity	NPC472534
0.7479	Intermediate Similarity	NPC27814
0.7478	Intermediate Similarity	NPC472702
0.7478	Intermediate Similarity	NPC472685
0.746	Intermediate Similarity	NPC475591
0.746	Intermediate Similarity	NPC213952
0.746	Intermediate Similarity	NPC312833
0.746	Intermediate Similarity	NPC187290
0.746	Intermediate Similarity	NPC21691
0.746	Intermediate Similarity	NPC236870
0.746	Intermediate Similarity	NPC80986
0.746	Intermediate Similarity	NPC313528
0.746	Intermediate Similarity	NPC4749
0.746	Intermediate Similarity	NPC10607
0.7459	Intermediate Similarity	NPC102088
0.7459	Intermediate Similarity	NPC474557
0.7459	Intermediate Similarity	NPC323821
0.7459	Intermediate Similarity	NPC143268
0.7459	Intermediate Similarity	NPC268238
0.7459	Intermediate Similarity	NPC473898
0.7459	Intermediate Similarity	NPC475633
0.7459	Intermediate Similarity	NPC471398
0.7459	Intermediate Similarity	NPC45218
0.7458	Intermediate Similarity	NPC230541
0.7458	Intermediate Similarity	NPC473169
0.7458	Intermediate Similarity	NPC293512
0.7456	Intermediate Similarity	NPC474724
0.7442	Intermediate Similarity	NPC475636
0.7442	Intermediate Similarity	NPC295220
0.744	Intermediate Similarity	NPC109973

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 NPC318751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	1772
0.2-0.3	4206
0.3-0.4	1966
0.4-0.5	561
0.5-0.6	221
0.6-0.7	157
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7724	Intermediate Similarity	NPD6054	Approved
0.76	Intermediate Similarity	NPD6370	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7578	Intermediate Similarity	NPD7736	Approved
0.754	Intermediate Similarity	NPD8328	Phase 3
0.752	Intermediate Similarity	NPD6016	Approved
0.752	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD7492	Approved
0.746	Intermediate Similarity	NPD5988	Approved
0.7422	Intermediate Similarity	NPD6616	Approved
0.7364	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7231	Intermediate Similarity	NPD8293	Discontinued
0.7176	Intermediate Similarity	NPD6033	Approved
0.7167	Intermediate Similarity	NPD6412	Phase 2
0.7165	Intermediate Similarity	NPD6319	Approved
0.7154	Intermediate Similarity	NPD8297	Approved
0.7107	Intermediate Similarity	NPD6881	Approved
0.7107	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD6402	Approved
0.7083	Intermediate Similarity	NPD5739	Approved
0.7083	Intermediate Similarity	NPD6675	Approved
0.7083	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6650	Approved
0.7073	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD6373	Approved
0.7049	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6992	Remote Similarity	NPD6883	Approved
0.6992	Remote Similarity	NPD7290	Approved
0.6992	Remote Similarity	NPD7102	Approved
0.6977	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD7320	Approved
0.6967	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6011	Approved
0.6935	Remote Similarity	NPD6847	Approved
0.6935	Remote Similarity	NPD6617	Approved
0.6935	Remote Similarity	NPD6869	Approved
0.6935	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD7902	Approved
0.6911	Remote Similarity	NPD6014	Approved
0.6911	Remote Similarity	NPD6013	Approved
0.6911	Remote Similarity	NPD6012	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6894	Remote Similarity	NPD7507	Approved
0.6885	Remote Similarity	NPD5701	Approved
0.6864	Remote Similarity	NPD5696	Approved
0.6855	Remote Similarity	NPD4634	Approved
0.6846	Remote Similarity	NPD8515	Approved
0.6846	Remote Similarity	NPD8517	Approved
0.6846	Remote Similarity	NPD8516	Approved
0.6846	Remote Similarity	NPD8513	Phase 3
0.681	Remote Similarity	NPD7748	Approved
0.6807	Remote Similarity	NPD5285	Approved
0.6807	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD5286	Approved
0.6803	Remote Similarity	NPD6008	Approved
0.68	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4755	Approved
0.675	Remote Similarity	NPD5223	Approved
0.6741	Remote Similarity	NPD7319	Approved
0.6724	Remote Similarity	NPD6399	Phase 3
0.6695	Remote Similarity	NPD5221	Approved
0.6695	Remote Similarity	NPD5222	Approved
0.6695	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4697	Phase 3
0.6694	Remote Similarity	NPD5224	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD5173	Approved
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD6084	Phase 2
0.6639	Remote Similarity	NPD5175	Approved
0.6639	Remote Similarity	NPD6083	Phase 2
0.6638	Remote Similarity	NPD7515	Phase 2
0.6638	Remote Similarity	NPD6079	Approved
0.6617	Remote Similarity	NPD6067	Discontinued
0.6615	Remote Similarity	NPD6335	Approved
0.661	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD5210	Approved
0.6609	Remote Similarity	NPD5328	Approved
0.6585	Remote Similarity	NPD5141	Approved
0.6579	Remote Similarity	NPD3573	Approved
0.6565	Remote Similarity	NPD7101	Approved
0.6565	Remote Similarity	NPD7100	Approved
0.6562	Remote Similarity	NPD8133	Approved
0.656	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD7260	Phase 2
0.6522	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD5737	Approved
0.6504	Remote Similarity	NPD4754	Approved
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD8035	Phase 2
0.6491	Remote Similarity	NPD3618	Phase 1
0.6489	Remote Similarity	NPD6313	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD5695	Phase 3
0.6466	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7503	Approved
0.6462	Remote Similarity	NPD6274	Approved
0.6462	Remote Similarity	NPD6868	Approved
0.6449	Remote Similarity	NPD5956	Approved
0.6446	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6406	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4768	Approved
0.64	Remote Similarity	NPD4767	Approved
0.6393	Remote Similarity	NPD7639	Approved
0.6393	Remote Similarity	NPD7640	Approved
0.6378	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD7327	Approved
0.6356	Remote Similarity	NPD5281	Approved
0.6356	Remote Similarity	NPD5694	Approved
0.6356	Remote Similarity	NPD6050	Approved
0.6356	Remote Similarity	NPD6411	Approved
0.6356	Remote Similarity	NPD5284	Approved
0.6348	Remote Similarity	NPD6098	Approved
0.6343	Remote Similarity	NPD6921	Approved
0.6343	Remote Similarity	NPD6908	Approved
0.6343	Remote Similarity	NPD6909	Approved
0.6333	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5135	Approved
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6328	Remote Similarity	NPD5247	Approved
0.6328	Remote Similarity	NPD5169	Approved
0.6328	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD6080	Approved
0.6325	Remote Similarity	NPD6904	Approved
0.6325	Remote Similarity	NPD4753	Phase 2
0.632	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7516	Approved
0.6316	Remote Similarity	NPD4786	Approved
0.6303	Remote Similarity	NPD4202	Approved
0.6299	Remote Similarity	NPD5128	Approved
0.6283	Remote Similarity	NPD3667	Approved
0.6279	Remote Similarity	NPD5215	Approved
0.6279	Remote Similarity	NPD5127	Approved
0.6279	Remote Similarity	NPD5216	Approved
0.6279	Remote Similarity	NPD5217	Approved
0.6271	Remote Similarity	NPD5692	Phase 3
0.6269	Remote Similarity	NPD8377	Approved
0.6269	Remote Similarity	NPD8294	Approved
0.6261	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6241	Remote Similarity	NPD6845	Suspended
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8335	Approved
0.6222	Remote Similarity	NPD8378	Approved
0.6222	Remote Similarity	NPD8296	Approved
0.6222	Remote Similarity	NPD8380	Approved
0.6222	Remote Similarity	NPD8033	Approved
0.6222	Remote Similarity	NPD8379	Approved
0.6207	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4694	Approved
0.6207	Remote Similarity	NPD5280	Approved
0.6207	Remote Similarity	NPD5279	Phase 3
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6101	Approved
0.6174	Remote Similarity	NPD4197	Approved
0.6172	Remote Similarity	NPD5168	Approved
0.6167	Remote Similarity	NPD5779	Approved
0.6167	Remote Similarity	NPD5778	Approved
0.6136	Remote Similarity	NPD5167	Approved
0.6134	Remote Similarity	NPD5207	Approved
0.6121	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4695	Discontinued
0.6106	Remote Similarity	NPD7525	Registered
0.6094	Remote Similarity	NPD6614	Approved
0.6094	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5693	Phase 1
0.6069	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7146	Approved
0.6068	Remote Similarity	NPD5330	Approved
0.6068	Remote Similarity	NPD7521	Approved
0.6068	Remote Similarity	NPD6409	Approved
0.6068	Remote Similarity	NPD6684	Approved
0.6068	Remote Similarity	NPD5690	Phase 2
0.6068	Remote Similarity	NPD7334	Approved
0.6048	Remote Similarity	NPD4225	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