NPASS Compound

Structure

NPC19679 OpenBabel07101719152D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.0933 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3373 -0.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9593 2.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9593 1.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3067 2.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1490 1.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2507 0.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3959 0.1947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8650 0.7433 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0102 -0.0568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7757 -0.3311 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4853 1.2691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9542 -1.3150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 23 1 0 0 0 0 6 21 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 2 1 6 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 18 13 1 6 0 0 0 18 19 1 0 0 0 0 19 24 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.22
Volume:	355.148
LogP:	4.265
LogD:	3.95
LogS:	-3.935
# Rotatable Bonds:	2
TPSA:	39.26
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	4.366
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.891
MDCK Permeability:	1.5018075828265864e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.386
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.907
Plasma Protein Binding (PPB):	80.70618438720703%
Volume Distribution (VD):	2.282
Pgp-substrate:	19.174772262573242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.574
CYP1A2-substrate:	0.911
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.45
CYP3A4-substrate:	0.841

ADMET: Excretion

Clearance (CL):	3.534
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.664
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.684
Carcinogencity:	0.317
Eye Corrosion:	0.018
Eye Irritation:	0.03
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: NPC19679

Natural Product ID:	NPC19679
*Common Name:**	9-Deacetylfumigaclavine C
IUPAC Name:	(6aR,9S,10S,10aR)-7,9-dimethyl-5-(2-methylbut-3-en-2-yl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-10-ol
Synonyms:	9-Deacetylfumigaclavine C
Standard InCHIKey:	VCXCXXJJHZVDSD-GJGHSUIPSA-N
Standard InCHI:	InChI=1S/C21H28N2O/c1-6-21(3,4)20-14-10-16-18(19(24)12(2)11-23(16)5)13-8-7-9-15(22-20)17(13)14/h6-9,12,16,18-19,22,24H,1,10-11H2,2-5H3/t12-,16+,18+,19-/m0/s1
SMILES:	C=CC(C)(C)c1c2C[C@@H]3[C@@H](c4cccc(c24)[nH]1)[C@H]([C@@H](C)CN3C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564377
PubChem CID:	42640472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002747] Clavines and derivatives

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	41000.0	nM	PMID[492902]

☑ 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 NPC19679 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	364
0.1-0.2	1844
0.2-0.3	10652
0.3-0.4	20780
0.4-0.5	4134
0.5-0.6	2678
0.6-0.7	1542
0.7-0.8	638
0.8-0.85	52
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC95783
0.9157	High Similarity	NPC189812
0.9157	High Similarity	NPC329688
0.8802	High Similarity	NPC317430
0.8757	High Similarity	NPC472123
0.869	High Similarity	NPC154293
0.8642	High Similarity	NPC33421
0.8639	High Similarity	NPC280548
0.8621	High Similarity	NPC472108
0.8621	High Similarity	NPC139291
0.8605	High Similarity	NPC151939
0.8538	High Similarity	NPC34508
0.8488	Intermediate Similarity	NPC37423
0.8488	Intermediate Similarity	NPC275305
0.8452	Intermediate Similarity	NPC16667
0.8434	Intermediate Similarity	NPC285469
0.8404	Intermediate Similarity	NPC87755
0.84	Intermediate Similarity	NPC300688
0.8391	Intermediate Similarity	NPC68354
0.8382	Intermediate Similarity	NPC472586
0.8363	Intermediate Similarity	NPC201700
0.8353	Intermediate Similarity	NPC470508
0.8343	Intermediate Similarity	NPC176199
0.8343	Intermediate Similarity	NPC270009
0.8343	Intermediate Similarity	NPC215795
0.8343	Intermediate Similarity	NPC472443
0.8324	Intermediate Similarity	NPC97525
0.8316	Intermediate Similarity	NPC475422
0.8314	Intermediate Similarity	NPC194411
0.8305	Intermediate Similarity	NPC472109
0.8305	Intermediate Similarity	NPC472110
0.8263	Intermediate Similarity	NPC207726
0.8258	Intermediate Similarity	NPC472294
0.8249	Intermediate Similarity	NPC192270
0.8235	Intermediate Similarity	NPC162730
0.8232	Intermediate Similarity	NPC329858
0.8225	Intermediate Similarity	NPC67056
0.822	Intermediate Similarity	NPC234999
0.8212	Intermediate Similarity	NPC476319
0.8207	Intermediate Similarity	NPC205403
0.8202	Intermediate Similarity	NPC472444
0.8172	Intermediate Similarity	NPC32200
0.8162	Intermediate Similarity	NPC229332
0.8138	Intermediate Similarity	NPC474116
0.8136	Intermediate Similarity	NPC133261
0.8132	Intermediate Similarity	NPC469501
0.8132	Intermediate Similarity	NPC469470
0.8128	Intermediate Similarity	NPC313985
0.8128	Intermediate Similarity	NPC49196
0.8128	Intermediate Similarity	NPC79129
0.8128	Intermediate Similarity	NPC249150
0.8128	Intermediate Similarity	NPC195461
0.8128	Intermediate Similarity	NPC81654
0.8125	Intermediate Similarity	NPC24594
0.8125	Intermediate Similarity	NPC472122
0.8118	Intermediate Similarity	NPC50503
0.8118	Intermediate Similarity	NPC56765
0.8095	Intermediate Similarity	NPC477135
0.8093	Intermediate Similarity	NPC475602
0.809	Intermediate Similarity	NPC198339
0.8079	Intermediate Similarity	NPC326575
0.8079	Intermediate Similarity	NPC293472
0.8045	Intermediate Similarity	NPC302191
0.8041	Intermediate Similarity	NPC475778
0.8033	Intermediate Similarity	NPC314333
0.8032	Intermediate Similarity	NPC249040
0.8021	Intermediate Similarity	NPC52557
0.8012	Intermediate Similarity	NPC230869
0.7989	Intermediate Similarity	NPC49954
0.7989	Intermediate Similarity	NPC472105
0.7989	Intermediate Similarity	NPC187827
0.7989	Intermediate Similarity	NPC474561
0.7978	Intermediate Similarity	NPC175474
0.7977	Intermediate Similarity	NPC311276
0.7957	Intermediate Similarity	NPC181502
0.7957	Intermediate Similarity	NPC85066
0.7956	Intermediate Similarity	NPC165201
0.7955	Intermediate Similarity	NPC158129
0.7943	Intermediate Similarity	NPC63751
0.7941	Intermediate Similarity	NPC470507
0.7938	Intermediate Similarity	NPC126066
0.7927	Intermediate Similarity	NPC475910
0.7923	Intermediate Similarity	NPC204565
0.7923	Intermediate Similarity	NPC317030
0.7923	Intermediate Similarity	NPC119700
0.7914	Intermediate Similarity	NPC231342
0.791	Intermediate Similarity	NPC313791
0.7907	Intermediate Similarity	NPC41257
0.7907	Intermediate Similarity	NPC206819
0.7907	Intermediate Similarity	NPC318065
0.7903	Intermediate Similarity	NPC474177
0.7895	Intermediate Similarity	NPC469785
0.7889	Intermediate Similarity	NPC15840
0.7886	Intermediate Similarity	NPC54988
0.7886	Intermediate Similarity	NPC160105
0.788	Intermediate Similarity	NPC173028
0.788	Intermediate Similarity	NPC46413
0.788	Intermediate Similarity	NPC65215
0.7874	Intermediate Similarity	NPC472587
0.7872	Intermediate Similarity	NPC232130
0.7861	Intermediate Similarity	NPC255229
0.7861	Intermediate Similarity	NPC81229
0.7857	Intermediate Similarity	NPC21605
0.7857	Intermediate Similarity	NPC477134
0.7849	Intermediate Similarity	NPC469762
0.7849	Intermediate Similarity	NPC286427
0.7845	Intermediate Similarity	NPC314394
0.7845	Intermediate Similarity	NPC233936
0.7842	Intermediate Similarity	NPC329747
0.7838	Intermediate Similarity	NPC472112
0.7836	Intermediate Similarity	NPC38736
0.7828	Intermediate Similarity	NPC251936
0.7818	Intermediate Similarity	NPC2949
0.7817	Intermediate Similarity	NPC478074
0.7816	Intermediate Similarity	NPC282231
0.7811	Intermediate Similarity	NPC37548
0.7809	Intermediate Similarity	NPC314603
0.7791	Intermediate Similarity	NPC184476
0.7791	Intermediate Similarity	NPC141353
0.7784	Intermediate Similarity	NPC246700
0.7784	Intermediate Similarity	NPC128751
0.7784	Intermediate Similarity	NPC34271
0.7778	Intermediate Similarity	NPC73952
0.7778	Intermediate Similarity	NPC469763
0.7778	Intermediate Similarity	NPC469786
0.7778	Intermediate Similarity	NPC25008
0.7778	Intermediate Similarity	NPC469760
0.7778	Intermediate Similarity	NPC469765
0.7778	Intermediate Similarity	NPC259644
0.7772	Intermediate Similarity	NPC474707
0.7771	Intermediate Similarity	NPC194640
0.7771	Intermediate Similarity	NPC473868
0.7771	Intermediate Similarity	NPC63157
0.7771	Intermediate Similarity	NPC40779
0.7766	Intermediate Similarity	NPC133366
0.7766	Intermediate Similarity	NPC195314
0.7759	Intermediate Similarity	NPC279918
0.7754	Intermediate Similarity	NPC55493
0.7754	Intermediate Similarity	NPC472113
0.7746	Intermediate Similarity	NPC129721
0.7744	Intermediate Similarity	NPC61637
0.7744	Intermediate Similarity	NPC314957
0.7742	Intermediate Similarity	NPC106833
0.7742	Intermediate Similarity	NPC206967
0.7742	Intermediate Similarity	NPC469497
0.7739	Intermediate Similarity	NPC469928
0.7739	Intermediate Similarity	NPC330009
0.7738	Intermediate Similarity	NPC264589
0.7737	Intermediate Similarity	NPC473747
0.7735	Intermediate Similarity	NPC6093
0.7735	Intermediate Similarity	NPC213468
0.7733	Intermediate Similarity	NPC70922
0.7733	Intermediate Similarity	NPC80597
0.7733	Intermediate Similarity	NPC75540
0.7733	Intermediate Similarity	NPC212376
0.7733	Intermediate Similarity	NPC211572
0.7722	Intermediate Similarity	NPC134586
0.7722	Intermediate Similarity	NPC288785
0.7717	Intermediate Similarity	NPC188387
0.7717	Intermediate Similarity	NPC163421
0.7711	Intermediate Similarity	NPC59084
0.7709	Intermediate Similarity	NPC471294
0.7708	Intermediate Similarity	NPC300183
0.7707	Intermediate Similarity	NPC470126
0.7706	Intermediate Similarity	NPC187951
0.7701	Intermediate Similarity	NPC6436
0.7701	Intermediate Similarity	NPC243716
0.7697	Intermediate Similarity	NPC243162
0.7696	Intermediate Similarity	NPC241024
0.7696	Intermediate Similarity	NPC476175
0.768	Intermediate Similarity	NPC59269
0.768	Intermediate Similarity	NPC211997
0.767	Intermediate Similarity	NPC102423
0.767	Intermediate Similarity	NPC253580
0.767	Intermediate Similarity	NPC90723
0.7663	Intermediate Similarity	NPC190007
0.7657	Intermediate Similarity	NPC215584
0.7657	Intermediate Similarity	NPC44773
0.7656	Intermediate Similarity	NPC329793
0.7656	Intermediate Similarity	NPC475151
0.7651	Intermediate Similarity	NPC88097
0.7637	Intermediate Similarity	NPC72980
0.7637	Intermediate Similarity	NPC219336
0.7634	Intermediate Similarity	NPC472323
0.7622	Intermediate Similarity	NPC94943
0.7622	Intermediate Similarity	NPC15102
0.7622	Intermediate Similarity	NPC198988
0.7611	Intermediate Similarity	NPC259545
0.7609	Intermediate Similarity	NPC48938
0.7609	Intermediate Similarity	NPC163055
0.7602	Intermediate Similarity	NPC124005
0.7594	Intermediate Similarity	NPC111602
0.7594	Intermediate Similarity	NPC196251
0.7594	Intermediate Similarity	NPC102338
0.7594	Intermediate Similarity	NPC63199
0.7592	Intermediate Similarity	NPC153042
0.7586	Intermediate Similarity	NPC51054
0.7582	Intermediate Similarity	NPC15573
0.7582	Intermediate Similarity	NPC217372
0.7582	Intermediate Similarity	NPC183662

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 NPC19679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	539
0.2-0.3	710
0.3-0.4	1553
0.4-0.5	2723
0.5-0.6	2439
0.6-0.7	827
0.7-0.8	149
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD5744	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD4076	Approved
0.8448	Intermediate Similarity	NPD4079	Approved
0.8439	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1325	Approved
0.8421	Intermediate Similarity	NPD1326	Approved
0.8391	Intermediate Similarity	NPD3506	Approved
0.8391	Intermediate Similarity	NPD3505	Approved
0.8128	Intermediate Similarity	NPD4600	Approved
0.8128	Intermediate Similarity	NPD4601	Approved
0.8046	Intermediate Similarity	NPD4639	Approved
0.8046	Intermediate Similarity	NPD4638	Approved
0.8046	Intermediate Similarity	NPD4640	Approved
0.8033	Intermediate Similarity	NPD4499	Approved
0.8011	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5254	Discontinued
0.7989	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD4181	Approved
0.7977	Intermediate Similarity	NPD3323	Discontinued
0.7966	Intermediate Similarity	NPD5065	Approved
0.7955	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD5021	Discontinued
0.7933	Intermediate Similarity	NPD8386	Phase 2
0.7826	Intermediate Similarity	NPD8431	Approved
0.7821	Intermediate Similarity	NPD2382	Approved
0.7821	Intermediate Similarity	NPD2380	Approved
0.7821	Intermediate Similarity	NPD2381	Approved
0.7797	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD5913	Phase 3
0.7796	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD6595	Phase 3
0.7789	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD3609	Approved
0.7753	Intermediate Similarity	NPD3610	Approved
0.7742	Intermediate Similarity	NPD6281	Approved
0.773	Intermediate Similarity	NPD2383	Phase 1
0.773	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2882	Phase 1
0.7714	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD5596	Phase 2
0.7705	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4128	Approved
0.7661	Intermediate Similarity	NPD4463	Approved
0.7661	Intermediate Similarity	NPD4462	Approved
0.7647	Intermediate Similarity	NPD4702	Approved
0.7647	Intermediate Similarity	NPD4703	Approved
0.7624	Intermediate Similarity	NPD4075	Phase 2
0.7617	Intermediate Similarity	NPD4511	Phase 1
0.7616	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6158	Phase 2
0.7588	Intermediate Similarity	NPD1683	Approved
0.7582	Intermediate Similarity	NPD2144	Approved
0.7554	Intermediate Similarity	NPD3038	Discontinued
0.7542	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5939	Approved
0.7538	Intermediate Similarity	NPD5936	Approved
0.7528	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5100	Phase 3
0.7515	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7418	Discontinued
0.7513	Intermediate Similarity	NPD2176	Approved
0.7513	Intermediate Similarity	NPD2175	Phase 3
0.7513	Intermediate Similarity	NPD2177	Approved
0.75	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7474	Suspended
0.7486	Intermediate Similarity	NPD6026	Approved
0.7474	Intermediate Similarity	NPD4500	Approved
0.7474	Intermediate Similarity	NPD4501	Approved
0.7474	Intermediate Similarity	NPD3404	Approved
0.7472	Intermediate Similarity	NPD5140	Approved
0.7472	Intermediate Similarity	NPD5138	Approved
0.7464	Intermediate Similarity	NPD7824	Approved
0.7456	Intermediate Similarity	NPD1592	Phase 3
0.7452	Intermediate Similarity	NPD6978	Phase 2
0.7452	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3961	Discontinued
0.7447	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7271	Approved
0.744	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5426	Phase 3
0.7409	Intermediate Similarity	NPD6664	Approved
0.7409	Intermediate Similarity	NPD5003	Discontinued
0.7387	Intermediate Similarity	NPD2916	Discontinued
0.7374	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7957	Phase 1
0.7374	Intermediate Similarity	NPD3003	Approved
0.7371	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7730	Approved
0.7368	Intermediate Similarity	NPD7731	Approved
0.7353	Intermediate Similarity	NPD1722	Approved
0.7349	Intermediate Similarity	NPD3385	Approved
0.7343	Intermediate Similarity	NPD6995	Phase 1
0.732	Intermediate Similarity	NPD7948	Phase 1
0.7318	Intermediate Similarity	NPD1684	Approved
0.7318	Intermediate Similarity	NPD1685	Approved
0.7318	Intermediate Similarity	NPD5315	Discontinued
0.7312	Intermediate Similarity	NPD5473	Discontinued
0.731	Intermediate Similarity	NPD3717	Discontinued
0.73	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3100	Discontinued
0.7287	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD482	Approved
0.7283	Intermediate Similarity	NPD6492	Phase 2
0.7282	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7935	Phase 2
0.7257	Intermediate Similarity	NPD2172	Phase 1
0.7253	Intermediate Similarity	NPD2844	Phase 3
0.725	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6227	Discontinued
0.7243	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5901	Discontinued
0.7235	Intermediate Similarity	NPD786	Approved
0.7234	Intermediate Similarity	NPD2092	Phase 2
0.7234	Intermediate Similarity	NPD2094	Phase 2
0.7234	Intermediate Similarity	NPD2095	Phase 2
0.7225	Intermediate Similarity	NPD1534	Approved
0.7219	Intermediate Similarity	NPD1262	Discovery
0.7214	Intermediate Similarity	NPD5658	Approved
0.7204	Intermediate Similarity	NPD8123	Approved
0.7204	Intermediate Similarity	NPD8122	Approved
0.7196	Intermediate Similarity	NPD2091	Phase 2
0.7196	Intermediate Similarity	NPD7952	Approved
0.7196	Intermediate Similarity	NPD7791	Approved
0.7196	Intermediate Similarity	NPD2096	Phase 2
0.7196	Intermediate Similarity	NPD7950	Approved
0.7196	Intermediate Similarity	NPD7951	Approved
0.7196	Intermediate Similarity	NPD7953	Approved
0.7196	Intermediate Similarity	NPD7789	Approved
0.7196	Intermediate Similarity	NPD7790	Approved
0.7192	Intermediate Similarity	NPD4502	Phase 2
0.7191	Intermediate Similarity	NPD2150	Discontinued
0.7186	Intermediate Similarity	NPD2920	Discontinued
0.7186	Intermediate Similarity	NPD6176	Phase 1
0.7186	Intermediate Similarity	NPD8072	Approved
0.7179	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2837	Discontinued
0.7173	Intermediate Similarity	NPD8020	Approved
0.7173	Intermediate Similarity	NPD8021	Approved
0.7171	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8322	Phase 2
0.7164	Intermediate Similarity	NPD6290	Phase 2
0.7158	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5862	Discovery
0.7158	Intermediate Similarity	NPD2640	Approved
0.7158	Intermediate Similarity	NPD2641	Approved
0.7157	Intermediate Similarity	NPD1768	Approved
0.715	Intermediate Similarity	NPD8272	Phase 2
0.7143	Intermediate Similarity	NPD7716	Approved
0.7143	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7717	Approved
0.7135	Intermediate Similarity	NPD7234	Approved
0.7135	Intermediate Similarity	NPD750	Phase 2
0.7135	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7233	Approved
0.7129	Intermediate Similarity	NPD6376	Discontinued
0.7128	Intermediate Similarity	NPD4602	Approved
0.7128	Intermediate Similarity	NPD7944	Discontinued
0.7122	Intermediate Similarity	NPD8094	Discontinued
0.7118	Intermediate Similarity	NPD6554	Approved
0.7118	Intermediate Similarity	NPD45	Approved
0.7115	Intermediate Similarity	NPD6455	Phase 3
0.7115	Intermediate Similarity	NPD7194	Discontinued
0.7114	Intermediate Similarity	NPD5530	Phase 1
0.7114	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3525	Discontinued
0.7108	Intermediate Similarity	NPD7470	Discontinued
0.7107	Intermediate Similarity	NPD53	Approved
0.7107	Intermediate Similarity	NPD7777	Approved
0.7107	Intermediate Similarity	NPD7778	Approved
0.7102	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD2565	Phase 2
0.7098	Intermediate Similarity	NPD2564	Approved
0.7087	Intermediate Similarity	NPD5903	Approved
0.7087	Intermediate Similarity	NPD5902	Approved
0.7083	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1038	Approved
0.7077	Intermediate Similarity	NPD802	Phase 2
0.7073	Intermediate Similarity	NPD8093	Discontinued
0.7073	Intermediate Similarity	NPD7455	Approved
0.7073	Intermediate Similarity	NPD7454	Approved
0.7073	Intermediate Similarity	NPD3330	Phase 1
0.7071	Intermediate Similarity	NPD3814	Phase 1
0.7071	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8115	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