NPASS Compound

Structure

NPC329911 OpenBabel07101719252D 31 35 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9234 2.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 21 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 17 6 1 1 0 0 0 17 23 1 0 0 0 0 17 25 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 20 2 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 26 1 1 0 0 0 24 31 1 0 0 0 0 25 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	425.18
Volume:	426.161
LogP:	2.09
LogD:	2.189
LogS:	-2.407
# Rotatable Bonds:	4
TPSA:	80.21
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	4.096
Fsp3:	0.417
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:	-5.675
MDCK Permeability:	4.262490983819589e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.81
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.66
Plasma Protein Binding (PPB):	73.50129699707031%
Volume Distribution (VD):	1.637
Pgp-substrate:	26.17974853515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.82
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	11.246
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.392
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.627
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC329911

Natural Product ID:	NPC329911
*Common Name:**	14Alpha-Hydroxyisocrebrine N-Oxide
IUPAC Name:	(13aS,14S)-3,4,6,7-tetramethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium-14-ol
Synonyms:	14Alpha-Hydroxyisocrebrine N-Oxide
Standard InCHIKey:	MSEYHQHYVWQFRE-ACYOWCCNSA-N
Standard InCHI:	InChI=1S/C24H27NO6/c1-28-18-8-7-13-21-16(12-25(27)9-5-6-17(25)23(21)26)14-10-19(29-2)20(30-3)11-15(14)22(13)24(18)31-4/h7-8,10-11,17,23,26H,5-6,9,12H2,1-4H3/t17-,23+,25?/m0/s1
SMILES:	COC1=C(C2=C(C=C1)C3=C(C[N+]4(CCCC4C3O)[O-])C5=CC(=C(C=C52)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1092162
PubChem CID:	15768065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7100.0	nM	PMID[557036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28000.0	nM	PMID[557036]

☑ 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 NPC329911 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	318
0.1-0.2	1456
0.2-0.3	5307
0.3-0.4	12441
0.4-0.5	5804
0.5-0.6	12524
0.6-0.7	3968
0.7-0.8	675
0.8-0.85	175
0.85-0.9	18
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC160570
0.9618	High Similarity	NPC76116
0.9437	High Similarity	NPC164429
0.9359	High Similarity	NPC477132
0.9359	High Similarity	NPC477133
0.8854	High Similarity	NPC44869
0.8824	High Similarity	NPC233718
0.8788	High Similarity	NPC150879
0.8606	High Similarity	NPC233650
0.8554	High Similarity	NPC134858
0.8452	Intermediate Similarity	NPC210140
0.8354	Intermediate Similarity	NPC244112
0.8344	Intermediate Similarity	NPC470924
0.8333	Intermediate Similarity	NPC169743
0.8286	Intermediate Similarity	NPC248642
0.8276	Intermediate Similarity	NPC126284
0.8239	Intermediate Similarity	NPC156576
0.8217	Intermediate Similarity	NPC210086
0.8204	Intermediate Similarity	NPC59028
0.8204	Intermediate Similarity	NPC92191
0.8155	Intermediate Similarity	NPC205167
0.8155	Intermediate Similarity	NPC249274
0.815	Intermediate Similarity	NPC2314
0.8144	Intermediate Similarity	NPC475326
0.8121	Intermediate Similarity	NPC37272
0.8107	Intermediate Similarity	NPC60186
0.8092	Intermediate Similarity	NPC470739
0.8092	Intermediate Similarity	NPC225597
0.8092	Intermediate Similarity	NPC477640
0.8084	Intermediate Similarity	NPC186063
0.8081	Intermediate Similarity	NPC158148
0.8081	Intermediate Similarity	NPC266176
0.8081	Intermediate Similarity	NPC58766
0.8081	Intermediate Similarity	NPC290759
0.8081	Intermediate Similarity	NPC82533
0.8081	Intermediate Similarity	NPC475686
0.8045	Intermediate Similarity	NPC214116
0.8036	Intermediate Similarity	NPC65490
0.8036	Intermediate Similarity	NPC148014
0.8036	Intermediate Similarity	NPC40389
0.8036	Intermediate Similarity	NPC315707
0.8036	Intermediate Similarity	NPC78359
0.8035	Intermediate Similarity	NPC474475
0.8025	Intermediate Similarity	NPC475828
0.8023	Intermediate Similarity	NPC145832
0.8023	Intermediate Similarity	NPC117188
0.8023	Intermediate Similarity	NPC205421
0.8023	Intermediate Similarity	NPC158376
0.8023	Intermediate Similarity	NPC306555
0.8023	Intermediate Similarity	NPC81218
0.8023	Intermediate Similarity	NPC12053
0.8023	Intermediate Similarity	NPC474931
0.8012	Intermediate Similarity	NPC13504
0.8012	Intermediate Similarity	NPC136508
0.8012	Intermediate Similarity	NPC253043
0.8012	Intermediate Similarity	NPC26601
0.8012	Intermediate Similarity	NPC96603
0.8012	Intermediate Similarity	NPC78222
0.8012	Intermediate Similarity	NPC196447
0.8012	Intermediate Similarity	NPC477563
0.8012	Intermediate Similarity	NPC306843
0.8012	Intermediate Similarity	NPC212794
0.7988	Intermediate Similarity	NPC130941
0.7976	Intermediate Similarity	NPC147091
0.7966	Intermediate Similarity	NPC244554
0.7953	Intermediate Similarity	NPC324144
0.7939	Intermediate Similarity	NPC219162
0.7929	Intermediate Similarity	NPC476572
0.7919	Intermediate Similarity	NPC181653
0.7919	Intermediate Similarity	NPC190332
0.7919	Intermediate Similarity	NPC100566
0.7917	Intermediate Similarity	NPC99659
0.7917	Intermediate Similarity	NPC325871
0.791	Intermediate Similarity	NPC118633
0.791	Intermediate Similarity	NPC320223
0.791	Intermediate Similarity	NPC148693
0.791	Intermediate Similarity	NPC477560
0.791	Intermediate Similarity	NPC294790
0.791	Intermediate Similarity	NPC114364
0.7898	Intermediate Similarity	NPC199465
0.7898	Intermediate Similarity	NPC128560
0.7898	Intermediate Similarity	NPC229166
0.7892	Intermediate Similarity	NPC274026
0.7877	Intermediate Similarity	NPC476575
0.7861	Intermediate Similarity	NPC124657
0.7861	Intermediate Similarity	NPC476432
0.7861	Intermediate Similarity	NPC24264
0.7853	Intermediate Similarity	NPC474470
0.7853	Intermediate Similarity	NPC241704
0.7849	Intermediate Similarity	NPC1229
0.7849	Intermediate Similarity	NPC320104
0.7836	Intermediate Similarity	NPC166014
0.7836	Intermediate Similarity	NPC4304
0.7836	Intermediate Similarity	NPC18402
0.7836	Intermediate Similarity	NPC27410
0.7824	Intermediate Similarity	NPC129603
0.7818	Intermediate Similarity	NPC253883
0.7818	Intermediate Similarity	NPC90844
0.7818	Intermediate Similarity	NPC476151
0.7818	Intermediate Similarity	NPC95075
0.7816	Intermediate Similarity	NPC247389
0.7816	Intermediate Similarity	NPC298979
0.7803	Intermediate Similarity	NPC302527
0.7803	Intermediate Similarity	NPC225774
0.7803	Intermediate Similarity	NPC167546
0.7803	Intermediate Similarity	NPC16805
0.7784	Intermediate Similarity	NPC10871
0.7784	Intermediate Similarity	NPC239775
0.7784	Intermediate Similarity	NPC57272
0.7772	Intermediate Similarity	NPC117717
0.7765	Intermediate Similarity	NPC323443
0.7765	Intermediate Similarity	NPC180756
0.7765	Intermediate Similarity	NPC32154
0.7759	Intermediate Similarity	NPC476002
0.7759	Intermediate Similarity	NPC219341
0.7753	Intermediate Similarity	NPC237044
0.7746	Intermediate Similarity	NPC124433
0.7746	Intermediate Similarity	NPC293871
0.774	Intermediate Similarity	NPC192135
0.774	Intermediate Similarity	NPC66341
0.774	Intermediate Similarity	NPC477020
0.7738	Intermediate Similarity	NPC81733
0.7738	Intermediate Similarity	NPC326316
0.7733	Intermediate Similarity	NPC97072
0.7733	Intermediate Similarity	NPC215829
0.7727	Intermediate Similarity	NPC168753
0.7727	Intermediate Similarity	NPC69712
0.7727	Intermediate Similarity	NPC118274
0.7727	Intermediate Similarity	NPC26240
0.7727	Intermediate Similarity	NPC477562
0.7725	Intermediate Similarity	NPC103379
0.7725	Intermediate Similarity	NPC477565
0.7714	Intermediate Similarity	NPC298186
0.7714	Intermediate Similarity	NPC252960
0.7714	Intermediate Similarity	NPC210918
0.7714	Intermediate Similarity	NPC301189
0.7709	Intermediate Similarity	NPC474325
0.7706	Intermediate Similarity	NPC127674
0.7706	Intermediate Similarity	NPC2413
0.7706	Intermediate Similarity	NPC5238
0.7706	Intermediate Similarity	NPC39701
0.7706	Intermediate Similarity	NPC278799
0.7706	Intermediate Similarity	NPC189266
0.7706	Intermediate Similarity	NPC184026
0.7706	Intermediate Similarity	NPC204828
0.7706	Intermediate Similarity	NPC249797
0.7706	Intermediate Similarity	NPC193949
0.7706	Intermediate Similarity	NPC110416
0.7706	Intermediate Similarity	NPC207757
0.7706	Intermediate Similarity	NPC276588
0.7706	Intermediate Similarity	NPC54379
0.7706	Intermediate Similarity	NPC469817
0.7706	Intermediate Similarity	NPC295691
0.7706	Intermediate Similarity	NPC172765
0.7701	Intermediate Similarity	NPC247972
0.7697	Intermediate Similarity	NPC304675
0.7697	Intermediate Similarity	NPC185838
0.7692	Intermediate Similarity	NPC82285
0.7692	Intermediate Similarity	NPC133011
0.768	Intermediate Similarity	NPC116284
0.7667	Intermediate Similarity	NPC474745
0.7667	Intermediate Similarity	NPC220961
0.7667	Intermediate Similarity	NPC267408
0.7667	Intermediate Similarity	NPC99179
0.7665	Intermediate Similarity	NPC476571
0.7665	Intermediate Similarity	NPC428
0.7665	Intermediate Similarity	NPC147390
0.7665	Intermediate Similarity	NPC135538
0.7665	Intermediate Similarity	NPC246587
0.7665	Intermediate Similarity	NPC24233
0.7661	Intermediate Similarity	NPC160931
0.7661	Intermediate Similarity	NPC37205
0.7657	Intermediate Similarity	NPC264850
0.7657	Intermediate Similarity	NPC13916
0.7644	Intermediate Similarity	NPC218614
0.7637	Intermediate Similarity	NPC135772
0.763	Intermediate Similarity	NPC160298
0.763	Intermediate Similarity	NPC271388
0.763	Intermediate Similarity	NPC205255
0.763	Intermediate Similarity	NPC477559
0.763	Intermediate Similarity	NPC266753
0.763	Intermediate Similarity	NPC119649
0.763	Intermediate Similarity	NPC235143
0.763	Intermediate Similarity	NPC230956
0.763	Intermediate Similarity	NPC232924
0.763	Intermediate Similarity	NPC306902
0.7627	Intermediate Similarity	NPC75958
0.7627	Intermediate Similarity	NPC311991
0.7624	Intermediate Similarity	NPC305847
0.7624	Intermediate Similarity	NPC155442
0.7624	Intermediate Similarity	NPC477561
0.7624	Intermediate Similarity	NPC312918
0.7624	Intermediate Similarity	NPC476574
0.7619	Intermediate Similarity	NPC92541
0.7619	Intermediate Similarity	NPC211296
0.7609	Intermediate Similarity	NPC237579
0.7605	Intermediate Similarity	NPC16107
0.7605	Intermediate Similarity	NPC179825
0.7605	Intermediate Similarity	NPC476144
0.7605	Intermediate Similarity	NPC191376

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 NPC329911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	679
0.2-0.3	960
0.3-0.4	2178
0.4-0.5	2606
0.5-0.6	1715
0.6-0.7	685
0.7-0.8	131
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8036	Intermediate Similarity	NPD2560	Approved
0.8036	Intermediate Similarity	NPD2563	Approved
0.7919	Intermediate Similarity	NPD2970	Approved
0.7919	Intermediate Similarity	NPD2969	Approved
0.7861	Intermediate Similarity	NPD6071	Discontinued
0.7771	Intermediate Similarity	NPD2489	Approved
0.7771	Intermediate Similarity	NPD27	Approved
0.7765	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3051	Approved
0.7636	Intermediate Similarity	NPD5241	Discontinued
0.7624	Intermediate Similarity	NPD7312	Approved
0.7624	Intermediate Similarity	NPD7310	Approved
0.7624	Intermediate Similarity	NPD7313	Approved
0.7624	Intermediate Similarity	NPD7311	Approved
0.7622	Intermediate Similarity	NPD4236	Phase 3
0.7622	Intermediate Similarity	NPD4237	Approved
0.7605	Intermediate Similarity	NPD4584	Approved
0.7582	Intermediate Similarity	NPD7309	Approved
0.7561	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD4663	Approved
0.7472	Intermediate Similarity	NPD4481	Phase 3
0.7472	Intermediate Similarity	NPD2898	Approved
0.7471	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4772	Phase 2
0.7442	Intermediate Similarity	NPD4773	Phase 2
0.7432	Intermediate Similarity	NPD4577	Approved
0.7432	Intermediate Similarity	NPD4578	Approved
0.7429	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7831	Phase 2
0.7429	Intermediate Similarity	NPD7833	Phase 2
0.7305	Intermediate Similarity	NPD3060	Approved
0.7257	Intermediate Similarity	NPD5772	Approved
0.7257	Intermediate Similarity	NPD5773	Approved
0.7204	Intermediate Similarity	NPD8053	Approved
0.7204	Intermediate Similarity	NPD8054	Approved
0.7193	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7400	Phase 3
0.7191	Intermediate Similarity	NPD5709	Phase 3
0.7179	Intermediate Similarity	NPD2972	Approved
0.7179	Intermediate Similarity	NPD3533	Approved
0.7159	Intermediate Similarity	NPD2978	Approved
0.7159	Intermediate Similarity	NPD2977	Approved
0.7158	Intermediate Similarity	NPD8156	Discontinued
0.7151	Intermediate Similarity	NPD6090	Discontinued
0.7151	Intermediate Similarity	NPD4666	Phase 3
0.715	Intermediate Similarity	NPD5676	Approved
0.7135	Intermediate Similarity	NPD2421	Approved
0.7135	Intermediate Similarity	NPD2420	Approved
0.7126	Intermediate Similarity	NPD4005	Discontinued
0.7118	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5976	Discontinued
0.7104	Intermediate Similarity	NPD8099	Discontinued
0.7104	Intermediate Similarity	NPD8251	Approved
0.7104	Intermediate Similarity	NPD8252	Approved
0.7098	Intermediate Similarity	NPD2974	Approved
0.7098	Intermediate Similarity	NPD2975	Approved
0.7098	Intermediate Similarity	NPD2973	Approved
0.7092	Intermediate Similarity	NPD3448	Approved
0.7092	Intermediate Similarity	NPD2491	Approved
0.7092	Intermediate Similarity	NPD3057	Approved
0.7079	Intermediate Similarity	NPD6788	Approved
0.7069	Intermediate Similarity	NPD4210	Discontinued
0.7055	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2493	Approved
0.7041	Intermediate Similarity	NPD2494	Approved
0.7041	Intermediate Similarity	NPD3452	Approved
0.7041	Intermediate Similarity	NPD3450	Approved
0.7029	Intermediate Similarity	NPD4017	Approved
0.7016	Intermediate Similarity	NPD2488	Approved
0.7016	Intermediate Similarity	NPD2490	Approved
0.7011	Intermediate Similarity	NPD6031	Approved
0.7011	Intermediate Similarity	NPD3641	Approved
0.7011	Intermediate Similarity	NPD3640	Phase 3
0.7011	Intermediate Similarity	NPD3639	Approved
0.7011	Intermediate Similarity	NPD6030	Approved
0.7006	Intermediate Similarity	NPD7298	Approved
0.7	Intermediate Similarity	NPD5177	Phase 3
0.6994	Remote Similarity	NPD4123	Phase 3
0.699	Remote Similarity	NPD4580	Approved
0.6978	Remote Similarity	NPD4010	Discontinued
0.6977	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2971	Approved
0.6968	Remote Similarity	NPD2968	Approved
0.6964	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6331	Phase 2
0.6944	Remote Similarity	NPD4055	Discovery
0.6941	Remote Similarity	NPD7037	Approved
0.6935	Remote Similarity	NPD4583	Approved
0.6935	Remote Similarity	NPD4582	Approved
0.6928	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD6107	Approved
0.6919	Remote Similarity	NPD2677	Approved
0.6901	Remote Similarity	NPD4162	Approved
0.6888	Remote Similarity	NPD4420	Approved
0.6884	Remote Similarity	NPD4002	Approved
0.6884	Remote Similarity	NPD4004	Approved
0.6882	Remote Similarity	NPD42	Phase 2
0.6882	Remote Similarity	NPD6042	Phase 2
0.6879	Remote Similarity	NPD6667	Approved
0.6879	Remote Similarity	NPD6666	Approved
0.6875	Remote Similarity	NPD3687	Approved
0.6875	Remote Similarity	NPD3686	Approved
0.6869	Remote Similarity	NPD4482	Phase 3
0.6868	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6072	Discontinued
0.6839	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1774	Approved
0.6836	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD3398	Discontinued
0.6821	Remote Similarity	NPD3692	Discontinued
0.6818	Remote Similarity	NPD4107	Approved
0.6809	Remote Similarity	NPD6297	Approved
0.6809	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1424	Approved
0.6798	Remote Similarity	NPD4675	Approved
0.6798	Remote Similarity	NPD4678	Approved
0.6793	Remote Similarity	NPD4166	Phase 2
0.6789	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5582	Discontinued
0.6782	Remote Similarity	NPD3845	Phase 1
0.6774	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2674	Phase 3
0.6766	Remote Similarity	NPD4475	Approved
0.6766	Remote Similarity	NPD4474	Approved
0.6765	Remote Similarity	NPD1753	Discontinued
0.6763	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7907	Approved
0.6757	Remote Similarity	NPD2388	Discontinued
0.6757	Remote Similarity	NPD6688	Approved
0.6757	Remote Similarity	NPD6687	Approved
0.6754	Remote Similarity	NPD6853	Approved
0.6754	Remote Similarity	NPD6851	Approved
0.675	Remote Similarity	NPD5006	Approved
0.675	Remote Similarity	NPD5005	Approved
0.6746	Remote Similarity	NPD4665	Approved
0.6746	Remote Similarity	NPD4111	Phase 1
0.6744	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6997	Phase 2
0.6724	Remote Similarity	NPD5160	Discontinued
0.6723	Remote Similarity	NPD1914	Approved
0.6707	Remote Similarity	NPD5718	Phase 2
0.6706	Remote Similarity	NPD6896	Approved
0.6706	Remote Similarity	NPD6895	Approved
0.6686	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7124	Phase 2
0.6686	Remote Similarity	NPD1375	Discontinued
0.6685	Remote Similarity	NPD2904	Discontinued
0.6684	Remote Similarity	NPD7039	Approved
0.6684	Remote Similarity	NPD7038	Approved
0.6683	Remote Similarity	NPD7047	Phase 3
0.6667	Remote Similarity	NPD2154	Approved
0.6667	Remote Similarity	NPD2156	Approved
0.6667	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2155	Approved
0.6649	Remote Similarity	NPD4157	Discontinued
0.6649	Remote Similarity	NPD7802	Discontinued
0.6648	Remote Similarity	NPD7213	Phase 3
0.6648	Remote Similarity	NPD7212	Phase 2
0.6648	Remote Similarity	NPD3124	Discontinued
0.6647	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2122	Discontinued
0.6628	Remote Similarity	NPD2161	Phase 2
0.6627	Remote Similarity	NPD3109	Approved
0.6627	Remote Similarity	NPD3110	Approved
0.662	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7280	Phase 3
0.6615	Remote Similarity	NPD7281	Phase 3
0.6615	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5312	Approved
0.6614	Remote Similarity	NPD5313	Approved
0.6613	Remote Similarity	NPD6747	Phase 1
0.661	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7020	Approved
0.661	Remote Similarity	NPD7447	Phase 1
0.661	Remote Similarity	NPD7019	Approved
0.6607	Remote Similarity	NPD598	Approved
0.6607	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3144	Approved
0.6607	Remote Similarity	NPD601	Approved
0.6607	Remote Similarity	NPD3145	Approved
0.6607	Remote Similarity	NPD597	Approved
0.6591	Remote Similarity	NPD7048	Phase 3
0.6585	Remote Similarity	NPD4859	Phase 1
0.6582	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD5604	Discontinued

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