NPASS Compound

Structure

CID17681 OpenBabel06191715342D 30 31 0 0 1 0 0 0 0 0999 V2000 -6.1297 -3.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -0.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -3.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2713 1.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8618 -2.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9958 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7278 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -0.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 0.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 -1.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9188 -0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5629 -0.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2278 0.3972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2637 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5368 -0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1297 -2.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -1.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -4.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7278 -1.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -2.6416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7996 0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0523 -0.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 0.3584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5317 -5.1416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7996 1.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7248 -1.6279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2278 0.3972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -3.6416 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 28 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 21 14 1 1 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 26 1 1 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 24 4 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.24
Volume:	443.47
LogP:	3.639
LogD:	3.49
LogS:	-4.619
# Rotatable Bonds:	12
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	4.456
Fsp3:	0.583
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:	-4.711
MDCK Permeability:	7.271001231856644e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.245
Human Intestinal Absorption (HIA):	0.578
20% Bioavailability (F20%):	0.24
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.438
Plasma Protein Binding (PPB):	89.62396240234375%
Volume Distribution (VD):	1.183
Pgp-substrate:	5.78920316696167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.213
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.529
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	8.649
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.189
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.263
Carcinogencity:	0.194
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC17681

Natural Product ID:	NPC17681
*Common Name:**	10-Acetylirciformonin B
IUPAC Name:	[(3E,6S,7E,11R)-1-(furan-3-yl)-11-hydroxy-4,8-dimethyl-11-[(2S)-2-methyl-5-oxooxolan-2-yl]undeca-3,7-dien-6-yl] acetate
Synonyms:	10-Acetylirciformonin B
Standard InCHIKey:	RGTRQKDHOCMNQZ-PRBWFTGVSA-N
Standard InCHI:	InChI=1S/C24H34O6/c1-17(6-5-7-20-11-13-28-16-20)14-21(29-19(3)25)15-18(2)8-9-22(26)24(4)12-10-23(27)30-24/h6,11,13,15-16,21-22,26H,5,7-10,12,14H2,1-4H3/b17-6+,18-15+/t21-,22+,24-/m0/s1
SMILES:	C/C(=CCCc1ccoc1)/C[C@@H](/C=C(C)/CC[C@H]([C@]1(C)CCC(=O)O1)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823121
PubChem CID:	54669795
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30704	Ircinia	Genus	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21902186]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	9600.0	nM	PMID[533351]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	200.0	nM	PMID[533351]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2200.0	nM	PMID[533351]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10600.0	nM	PMID[533351]

☑ 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 NPC17681 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	250
0.1-0.2	1030
0.2-0.3	3353
0.3-0.4	7994
0.4-0.5	11660
0.5-0.6	8896
0.6-0.7	8563
0.7-0.8	843
0.8-0.85	79
0.85-0.9	20
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC97740
0.976	High Similarity	NPC45358
0.9516	High Similarity	NPC471501
0.9516	High Similarity	NPC137570
0.9516	High Similarity	NPC471554
0.9516	High Similarity	NPC473355
0.9516	High Similarity	NPC471573
0.9206	High Similarity	NPC476016
0.92	High Similarity	NPC471559
0.9127	High Similarity	NPC329694
0.9127	High Similarity	NPC474260
0.9127	High Similarity	NPC329922
0.9127	High Similarity	NPC81912
0.9055	High Similarity	NPC474830
0.8984	High Similarity	NPC474438
0.8984	High Similarity	NPC474279
0.8898	High Similarity	NPC474829
0.8898	High Similarity	NPC71274
0.8898	High Similarity	NPC75557
0.8889	High Similarity	NPC475818
0.8855	High Similarity	NPC471545
0.8855	High Similarity	NPC471544
0.8855	High Similarity	NPC473344
0.881	High Similarity	NPC473379
0.881	High Similarity	NPC471549
0.88	High Similarity	NPC474817
0.874	High Similarity	NPC476351
0.871	High Similarity	NPC208906
0.871	High Similarity	NPC144745
0.8661	High Similarity	NPC289911
0.8661	High Similarity	NPC283284
0.8657	High Similarity	NPC14650
0.8647	High Similarity	NPC474426
0.8647	High Similarity	NPC474425
0.8647	High Similarity	NPC474407
0.8593	High Similarity	NPC303217
0.8583	High Similarity	NPC474136
0.8582	High Similarity	NPC288209
0.8425	Intermediate Similarity	NPC473969
0.8406	Intermediate Similarity	NPC107571
0.8406	Intermediate Similarity	NPC90953
0.8394	Intermediate Similarity	NPC473268
0.8394	Intermediate Similarity	NPC186626
0.8369	Intermediate Similarity	NPC251865
0.8369	Intermediate Similarity	NPC307346
0.8369	Intermediate Similarity	NPC137295
0.8369	Intermediate Similarity	NPC261733
0.8369	Intermediate Similarity	NPC218712
0.8369	Intermediate Similarity	NPC267004
0.8333	Intermediate Similarity	NPC125182
0.8333	Intermediate Similarity	NPC69647
0.8306	Intermediate Similarity	NPC26157
0.8306	Intermediate Similarity	NPC1811
0.8299	Intermediate Similarity	NPC296807
0.8299	Intermediate Similarity	NPC155939
0.8299	Intermediate Similarity	NPC141538
0.8298	Intermediate Similarity	NPC80635
0.8288	Intermediate Similarity	NPC268905
0.8288	Intermediate Similarity	NPC474378
0.8288	Intermediate Similarity	NPC474219
0.8268	Intermediate Similarity	NPC131801
0.8264	Intermediate Similarity	NPC7388
0.8254	Intermediate Similarity	NPC28054
0.8252	Intermediate Similarity	NPC104924
0.8244	Intermediate Similarity	NPC65735
0.8244	Intermediate Similarity	NPC188377
0.8227	Intermediate Similarity	NPC121158
0.8226	Intermediate Similarity	NPC105249
0.8222	Intermediate Similarity	NPC89133
0.8207	Intermediate Similarity	NPC234494
0.8194	Intermediate Similarity	NPC255414
0.8194	Intermediate Similarity	NPC250228
0.8188	Intermediate Similarity	NPC472776
0.8188	Intermediate Similarity	NPC197137
0.8188	Intermediate Similarity	NPC472777
0.8188	Intermediate Similarity	NPC472778
0.8176	Intermediate Similarity	NPC214541
0.8176	Intermediate Similarity	NPC44675
0.8169	Intermediate Similarity	NPC254198
0.8154	Intermediate Similarity	NPC1848
0.8154	Intermediate Similarity	NPC79557
0.8151	Intermediate Similarity	NPC196846
0.8148	Intermediate Similarity	NPC21460
0.8133	Intermediate Similarity	NPC475967
0.8133	Intermediate Similarity	NPC472779
0.813	Intermediate Similarity	NPC473356
0.813	Intermediate Similarity	NPC471521
0.8129	Intermediate Similarity	NPC170604
0.8129	Intermediate Similarity	NPC215109
0.8106	Intermediate Similarity	NPC243269
0.8092	Intermediate Similarity	NPC263870
0.8092	Intermediate Similarity	NPC477967
0.8085	Intermediate Similarity	NPC67003
0.8082	Intermediate Similarity	NPC195325
0.8082	Intermediate Similarity	NPC472654
0.8069	Intermediate Similarity	NPC471174
0.8069	Intermediate Similarity	NPC216755
0.8067	Intermediate Similarity	NPC45101
0.8067	Intermediate Similarity	NPC36655
0.8067	Intermediate Similarity	NPC261597
0.8067	Intermediate Similarity	NPC187149
0.8067	Intermediate Similarity	NPC470118
0.8067	Intermediate Similarity	NPC299038
0.8065	Intermediate Similarity	NPC177331
0.806	Intermediate Similarity	NPC95567
0.806	Intermediate Similarity	NPC319140
0.8056	Intermediate Similarity	NPC5676
0.8054	Intermediate Similarity	NPC92979
0.8041	Intermediate Similarity	NPC294511
0.8041	Intermediate Similarity	NPC44577
0.8041	Intermediate Similarity	NPC33938
0.8041	Intermediate Similarity	NPC470996
0.8041	Intermediate Similarity	NPC121615
0.8041	Intermediate Similarity	NPC75906
0.8029	Intermediate Similarity	NPC471817
0.8027	Intermediate Similarity	NPC470997
0.8026	Intermediate Similarity	NPC470792
0.8013	Intermediate Similarity	NPC475226
0.8013	Intermediate Similarity	NPC84349
0.8013	Intermediate Similarity	NPC472671
0.8	Intermediate Similarity	NPC475864
0.8	Intermediate Similarity	NPC346
0.8	Intermediate Similarity	NPC469485
0.8	Intermediate Similarity	NPC4898
0.7987	Intermediate Similarity	NPC34421
0.7987	Intermediate Similarity	NPC57998
0.7987	Intermediate Similarity	NPC98206
0.7987	Intermediate Similarity	NPC237259
0.7986	Intermediate Similarity	NPC476947
0.7985	Intermediate Similarity	NPC46536
0.7985	Intermediate Similarity	NPC138139
0.7974	Intermediate Similarity	NPC283209
0.7973	Intermediate Similarity	NPC18135
0.797	Intermediate Similarity	NPC118853
0.7961	Intermediate Similarity	NPC477402
0.7961	Intermediate Similarity	NPC470789
0.7959	Intermediate Similarity	NPC471001
0.7958	Intermediate Similarity	NPC90296
0.7958	Intermediate Similarity	NPC282973
0.7956	Intermediate Similarity	NPC298190
0.7947	Intermediate Similarity	NPC475066
0.7947	Intermediate Similarity	NPC214495
0.7947	Intermediate Similarity	NPC470119
0.7947	Intermediate Similarity	NPC173544
0.7947	Intermediate Similarity	NPC194499
0.7935	Intermediate Similarity	NPC472651
0.7933	Intermediate Similarity	NPC264943
0.7931	Intermediate Similarity	NPC34056
0.7931	Intermediate Similarity	NPC195920
0.7926	Intermediate Similarity	NPC83178
0.7923	Intermediate Similarity	NPC21831
0.7923	Intermediate Similarity	NPC187547
0.7922	Intermediate Similarity	NPC123088
0.7917	Intermediate Similarity	NPC267632
0.7917	Intermediate Similarity	NPC223415
0.7917	Intermediate Similarity	NPC470741
0.7917	Intermediate Similarity	NPC243577
0.7914	Intermediate Similarity	NPC106247
0.791	Intermediate Similarity	NPC179354
0.7908	Intermediate Similarity	NPC200782
0.7908	Intermediate Similarity	NPC263432
0.7905	Intermediate Similarity	NPC228842
0.7895	Intermediate Similarity	NPC262872
0.7891	Intermediate Similarity	NPC471007
0.7891	Intermediate Similarity	NPC474255
0.7891	Intermediate Similarity	NPC471618
0.7891	Intermediate Similarity	NPC474220
0.7885	Intermediate Similarity	NPC472652
0.7885	Intermediate Similarity	NPC271235
0.7871	Intermediate Similarity	NPC472141
0.7868	Intermediate Similarity	NPC112706
0.7868	Intermediate Similarity	NPC207294
0.7867	Intermediate Similarity	NPC253201
0.7867	Intermediate Similarity	NPC302054
0.7862	Intermediate Similarity	NPC476944
0.7862	Intermediate Similarity	NPC86935
0.7857	Intermediate Similarity	NPC285567
0.7857	Intermediate Similarity	NPC158525
0.7857	Intermediate Similarity	NPC92941
0.7857	Intermediate Similarity	NPC472773
0.7857	Intermediate Similarity	NPC477405
0.7852	Intermediate Similarity	NPC291150
0.7852	Intermediate Similarity	NPC116717
0.7847	Intermediate Similarity	NPC184053
0.7843	Intermediate Similarity	NPC335761
0.7842	Intermediate Similarity	NPC218838
0.7838	Intermediate Similarity	NPC475904
0.7838	Intermediate Similarity	NPC470998
0.7838	Intermediate Similarity	NPC474270
0.7834	Intermediate Similarity	NPC82602
0.7829	Intermediate Similarity	NPC7059
0.7829	Intermediate Similarity	NPC304692
0.7829	Intermediate Similarity	NPC88007
0.7823	Intermediate Similarity	NPC476938
0.7823	Intermediate Similarity	NPC476937
0.7823	Intermediate Similarity	NPC302987
0.7823	Intermediate Similarity	NPC221809
0.7821	Intermediate Similarity	NPC476850
0.7821	Intermediate Similarity	NPC100333
0.7821	Intermediate Similarity	NPC476861

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 NPC17681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	899
0.2-0.3	2217
0.3-0.4	2678
0.4-0.5	1958
0.5-0.6	916
0.6-0.7	252
0.7-0.8	12
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	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD5761	Phase 2
0.7582	Intermediate Similarity	NPD5760	Phase 2
0.7279	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8434	Phase 2
0.7185	Intermediate Similarity	NPD9092	Discovery
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6799	Approved
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7042	Intermediate Similarity	NPD5647	Approved
0.7027	Intermediate Similarity	NPD7033	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD6765	Approved
0.7006	Intermediate Similarity	NPD6764	Approved
0.7	Intermediate Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD2354	Approved
0.6974	Remote Similarity	NPD3887	Approved
0.6968	Remote Similarity	NPD920	Approved
0.6966	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6801	Discontinued
0.6944	Remote Similarity	NPD6832	Phase 2
0.6943	Remote Similarity	NPD6599	Discontinued
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9717	Approved
0.6879	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD9494	Approved
0.6859	Remote Similarity	NPD5403	Approved
0.6842	Remote Similarity	NPD6785	Approved
0.6842	Remote Similarity	NPD6784	Approved
0.6839	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5401	Approved
0.6832	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2344	Approved
0.6821	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6005	Phase 3
0.6821	Remote Similarity	NPD6002	Phase 3
0.6821	Remote Similarity	NPD6004	Phase 3
0.6821	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6559	Discontinued
0.6803	Remote Similarity	NPD6233	Phase 2
0.6803	Remote Similarity	NPD4062	Phase 3
0.68	Remote Similarity	NPD2799	Discontinued
0.6791	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6653	Approved
0.6755	Remote Similarity	NPD1551	Phase 2
0.6748	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD919	Approved
0.6747	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2313	Discontinued
0.6735	Remote Similarity	NPD3764	Approved
0.6728	Remote Similarity	NPD3882	Suspended
0.6711	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD447	Suspended
0.6711	Remote Similarity	NPD2353	Approved
0.6708	Remote Similarity	NPD7819	Suspended
0.6691	Remote Similarity	NPD7843	Approved
0.6689	Remote Similarity	NPD4308	Phase 3
0.6688	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD3749	Approved
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD17	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD2309	Approved
0.6642	Remote Similarity	NPD1241	Discontinued
0.6642	Remote Similarity	NPD2684	Approved
0.6625	Remote Similarity	NPD4380	Phase 2
0.6624	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7097	Phase 1
0.6623	Remote Similarity	NPD1243	Approved
0.6622	Remote Similarity	NPD3268	Approved
0.6621	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1203	Approved
0.6621	Remote Similarity	NPD6362	Approved
0.6621	Remote Similarity	NPD2797	Approved
0.6601	Remote Similarity	NPD5763	Approved
0.6601	Remote Similarity	NPD5762	Approved
0.6601	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.66	Remote Similarity	NPD230	Phase 1
0.6594	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5049	Phase 3
0.6581	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1019	Discontinued
0.6573	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2163	Approved
0.6567	Remote Similarity	NPD1358	Approved
0.6564	Remote Similarity	NPD3817	Phase 2
0.6562	Remote Similarity	NPD7458	Discontinued
0.6558	Remote Similarity	NPD2424	Discontinued
0.6554	Remote Similarity	NPD7095	Approved
0.6549	Remote Similarity	NPD1778	Approved
0.6547	Remote Similarity	NPD7157	Approved
0.6543	Remote Similarity	NPD1934	Approved
0.6541	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2240	Approved
0.6536	Remote Similarity	NPD2239	Approved
0.6533	Remote Similarity	NPD4307	Phase 2
0.6529	Remote Similarity	NPD5844	Phase 1
0.6528	Remote Similarity	NPD3972	Approved
0.6525	Remote Similarity	NPD1894	Discontinued
0.6519	Remote Similarity	NPD2533	Approved
0.6519	Remote Similarity	NPD2534	Approved
0.6519	Remote Similarity	NPD4661	Approved
0.6519	Remote Similarity	NPD4662	Approved
0.6519	Remote Similarity	NPD2532	Approved
0.6512	Remote Similarity	NPD7685	Pre-registration
0.6503	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7440	Discontinued
0.6494	Remote Similarity	NPD2346	Discontinued
0.6494	Remote Similarity	NPD1471	Phase 3
0.649	Remote Similarity	NPD1933	Approved
0.6481	Remote Similarity	NPD6386	Approved
0.6481	Remote Similarity	NPD6385	Approved
0.6474	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3750	Approved
0.6474	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD2067	Discontinued
0.6467	Remote Similarity	NPD8127	Discontinued
0.6467	Remote Similarity	NPD7199	Phase 2
0.6467	Remote Similarity	NPD1247	Approved
0.646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3226	Approved
0.6457	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5958	Discontinued
0.6452	Remote Similarity	NPD4534	Discontinued
0.6444	Remote Similarity	NPD290	Approved
0.6433	Remote Similarity	NPD6190	Approved
0.6433	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2935	Discontinued
0.6429	Remote Similarity	NPD6808	Phase 2
0.6424	Remote Similarity	NPD7768	Phase 2
0.6424	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3142	Approved
0.6424	Remote Similarity	NPD1240	Approved
0.6424	Remote Similarity	NPD3140	Approved
0.6415	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5494	Approved
0.6402	Remote Similarity	NPD8455	Phase 2
0.6402	Remote Similarity	NPD2801	Approved
0.64	Remote Similarity	NPD411	Approved
0.6397	Remote Similarity	NPD2182	Approved
0.6395	Remote Similarity	NPD3266	Approved
0.6395	Remote Similarity	NPD3267	Approved
0.6395	Remote Similarity	NPD7074	Phase 3
0.6392	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3496	Discontinued
0.6383	Remote Similarity	NPD9493	Approved
0.6382	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.638	Remote Similarity	NPD958	Approved
0.6375	Remote Similarity	NPD2186	Approved
0.637	Remote Similarity	NPD3134	Approved
0.6364	Remote Similarity	NPD3748	Approved
0.6364	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1510	Phase 2
0.6358	Remote Similarity	NPD2649	Approved
0.6358	Remote Similarity	NPD2651	Approved
0.6353	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6166	Phase 2
0.6353	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2798	Approved
0.6346	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8312	Approved
0.6343	Remote Similarity	NPD8313	Approved
0.634	Remote Similarity	NPD1607	Approved
0.6337	Remote Similarity	NPD7054	Approved
0.6333	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3225	Approved
0.6325	Remote Similarity	NPD4966	Approved
0.6325	Remote Similarity	NPD4967	Phase 2
0.6325	Remote Similarity	NPD4965	Approved
0.6324	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6032	Approved
0.6306	Remote Similarity	NPD1652	Phase 2
0.6303	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1481	Phase 2
0.6301	Remote Similarity	NPD7472	Approved
0.6294	Remote Similarity	NPD3926	Phase 2
0.6294	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.628	Remote Similarity	NPD6677	Suspended
0.6278	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD3847	Discontinued
0.6275	Remote Similarity	NPD5124	Phase 1
0.6275	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4340	Discontinued
0.6265	Remote Similarity	NPD5353	Approved
0.6257	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3451	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