NPASS Compound

Structure

CID148709 OpenBabel06191715522D 22 25 0 0 1 0 0 0 0 0999 V2000 -2.4915 -0.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7891 1.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1687 -2.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1857 -1.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3606 -3.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3945 -1.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5970 -1.8284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6010 -2.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7817 -3.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5695 -2.7640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5864 -1.8407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7990 -1.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0112 -2.7548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0108 -1.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7935 -1.3775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7923 -0.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7882 -0.4605 0.0000 C 0 0 0 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 0.8128 -3.2008 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5854 0.0123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5786 -0.0038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 0.9117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.14
Volume:	307.207
LogP:	1.781
LogD:	1.956
LogS:	-1.474
# Rotatable Bonds:	2
TPSA:	50.72
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.895
Synthetic Accessibility Score:	3.118
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.033
MDCK Permeability:	1.9410143067943864e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	77.03697967529297%
Volume Distribution (VD):	1.539
Pgp-substrate:	10.548700332641602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.683
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.658
CYP2D6-inhibitor:	0.423
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.845

ADMET: Excretion

Clearance (CL):	2.671
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.474
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.364
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC148709

Natural Product ID:	NPC148709
*Common Name:**	3-Hydroxynornuciferine
IUPAC Name:	(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3-ol
Synonyms:	3-Hydroxynornuciferine
Standard InCHIKey:	AOGVVFDNSYRXJL-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-21-17-15-11-6-4-3-5-10(11)9-13-14(15)12(7-8-19-13)16(20)18(17)22-2/h3-6,13,19-20H,7-9H2,1-2H3/t13-/m1/s1
SMILES:	COc1c2-c3ccccc3C[C@@H]3c2c(CCN3)c(c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461698
PubChem CID:	158223
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO33299	guatteria foliosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964785]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15887	Absidia orchidis	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11373	0nomuraea spiralis	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12992	Shigella boydii	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17964	Aspergillus subolivaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13646	Phlebia strigosozonata	Species	Meruliaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	68.2	%	PMID[461300]

☑ 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 NPC148709 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	353
0.1-0.2	1838
0.2-0.3	8959
0.3-0.4	9145
0.4-0.5	5986
0.5-0.6	10721
0.6-0.7	4517
0.7-0.8	848
0.8-0.85	200
0.85-0.9	85
0.9-0.95	40
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476577
1.0	High Similarity	NPC173416
0.9877	High Similarity	NPC474507
0.9627	High Similarity	NPC168753
0.9627	High Similarity	NPC118274
0.9509	High Similarity	NPC66341
0.9509	High Similarity	NPC192135
0.9509	High Similarity	NPC477020
0.9506	High Similarity	NPC69712
0.9506	High Similarity	NPC26240
0.9506	High Similarity	NPC477562
0.9448	High Similarity	NPC239775
0.9441	High Similarity	NPC81247
0.9441	High Similarity	NPC35627
0.9441	High Similarity	NPC476573
0.9408	High Similarity	NPC476576
0.9408	High Similarity	NPC186546
0.9383	High Similarity	NPC204947
0.9235	High Similarity	NPC57036
0.9162	High Similarity	NPC112575
0.9146	High Similarity	NPC205421
0.9146	High Similarity	NPC117188
0.9146	High Similarity	NPC12053
0.9146	High Similarity	NPC306555
0.9146	High Similarity	NPC474931
0.9146	High Similarity	NPC145832
0.9146	High Similarity	NPC81218
0.9146	High Similarity	NPC158376
0.9141	High Similarity	NPC477563
0.9141	High Similarity	NPC78222
0.9141	High Similarity	NPC196447
0.9141	High Similarity	NPC212794
0.9141	High Similarity	NPC306843
0.9141	High Similarity	NPC13504
0.9141	High Similarity	NPC96603
0.9141	High Similarity	NPC253043
0.9141	High Similarity	NPC136508
0.9118	High Similarity	NPC135772
0.9112	High Similarity	NPC155442
0.9112	High Similarity	NPC477561
0.9112	High Similarity	NPC312918
0.9112	High Similarity	NPC476574
0.908	High Similarity	NPC324144
0.908	High Similarity	NPC1229
0.9074	High Similarity	NPC27410
0.9074	High Similarity	NPC166014
0.9023	High Similarity	NPC117717
0.9006	High Similarity	NPC203784
0.9006	High Similarity	NPC170503
0.9006	High Similarity	NPC126519
0.9	High Similarity	NPC474506
0.9	High Similarity	NPC32413
0.8994	High Similarity	NPC23219
0.8988	High Similarity	NPC477558
0.897	High Similarity	NPC56887
0.897	High Similarity	NPC193853
0.897	High Similarity	NPC223077
0.8941	High Similarity	NPC258695
0.8941	High Similarity	NPC470879
0.8909	High Similarity	NPC209377
0.8876	High Similarity	NPC329969
0.8855	High Similarity	NPC264850
0.8855	High Similarity	NPC13916
0.881	High Similarity	NPC152212
0.8807	High Similarity	NPC478093
0.88	High Similarity	NPC82763
0.8795	High Similarity	NPC24465
0.8772	High Similarity	NPC320223
0.8772	High Similarity	NPC114364
0.8765	High Similarity	NPC128560
0.8765	High Similarity	NPC199465
0.8765	High Similarity	NPC229166
0.8765	High Similarity	NPC477564
0.8765	High Similarity	NPC2295
0.8758	High Similarity	NPC277669
0.8758	High Similarity	NPC76213
0.8757	High Similarity	NPC231371
0.8757	High Similarity	NPC478091
0.8757	High Similarity	NPC30182
0.8757	High Similarity	NPC473589
0.8757	High Similarity	NPC478092
0.872	High Similarity	NPC79328
0.872	High Similarity	NPC476572
0.8712	High Similarity	NPC325871
0.8712	High Similarity	NPC99659
0.8698	High Similarity	NPC6152
0.8693	High Similarity	NPC11296
0.8693	High Similarity	NPC274661
0.8693	High Similarity	NPC175890
0.8693	High Similarity	NPC82457
0.8693	High Similarity	NPC48490
0.8686	High Similarity	NPC214116
0.8675	High Similarity	NPC60186
0.8667	High Similarity	NPC7393
0.8652	High Similarity	NPC256124
0.8647	High Similarity	NPC149090
0.8647	High Similarity	NPC19520
0.8644	High Similarity	NPC60295
0.8644	High Similarity	NPC191132
0.8644	High Similarity	NPC475754
0.8642	High Similarity	NPC326316
0.8642	High Similarity	NPC81733
0.8639	High Similarity	NPC204908
0.8639	High Similarity	NPC83198
0.8634	High Similarity	NPC60538
0.8634	High Similarity	NPC207824
0.8631	High Similarity	NPC195392
0.8631	High Similarity	NPC86144
0.8631	High Similarity	NPC304659
0.8621	High Similarity	NPC476575
0.8614	High Similarity	NPC230956
0.8614	High Similarity	NPC205255
0.8614	High Similarity	NPC271388
0.8614	High Similarity	NPC119649
0.8614	High Similarity	NPC235143
0.858	High Similarity	NPC298979
0.8563	High Similarity	NPC79402
0.8563	High Similarity	NPC80759
0.8554	High Similarity	NPC221864
0.8545	High Similarity	NPC29647
0.8531	High Similarity	NPC22115
0.8531	High Similarity	NPC275680
0.8521	High Similarity	NPC68328
0.8514	High Similarity	NPC116284
0.8512	High Similarity	NPC189470
0.8506	High Similarity	NPC267408
0.8488	Intermediate Similarity	NPC232386
0.8488	Intermediate Similarity	NPC152680
0.8488	Intermediate Similarity	NPC190783
0.8476	Intermediate Similarity	NPC114124
0.8462	Intermediate Similarity	NPC225774
0.8457	Intermediate Similarity	NPC286119
0.8418	Intermediate Similarity	NPC95426
0.8418	Intermediate Similarity	NPC302245
0.8418	Intermediate Similarity	NPC16357
0.8412	Intermediate Similarity	NPC24264
0.8412	Intermediate Similarity	NPC219341
0.8412	Intermediate Similarity	NPC476432
0.8409	Intermediate Similarity	NPC229373
0.8409	Intermediate Similarity	NPC49075
0.8409	Intermediate Similarity	NPC290005
0.8409	Intermediate Similarity	NPC181796
0.8409	Intermediate Similarity	NPC90998
0.8409	Intermediate Similarity	NPC223690
0.8409	Intermediate Similarity	NPC7715
0.8409	Intermediate Similarity	NPC311973
0.8409	Intermediate Similarity	NPC30779
0.8409	Intermediate Similarity	NPC328155
0.8409	Intermediate Similarity	NPC185639
0.8409	Intermediate Similarity	NPC8836
0.8409	Intermediate Similarity	NPC42663
0.8409	Intermediate Similarity	NPC271013
0.8409	Intermediate Similarity	NPC251735
0.8409	Intermediate Similarity	NPC104196
0.8409	Intermediate Similarity	NPC222661
0.8409	Intermediate Similarity	NPC279228
0.8409	Intermediate Similarity	NPC54654
0.8409	Intermediate Similarity	NPC285931
0.8409	Intermediate Similarity	NPC182052
0.8409	Intermediate Similarity	NPC258657
0.8409	Intermediate Similarity	NPC239824
0.8409	Intermediate Similarity	NPC290582
0.8409	Intermediate Similarity	NPC217748
0.8409	Intermediate Similarity	NPC15414
0.8405	Intermediate Similarity	NPC103379
0.8405	Intermediate Similarity	NPC477565
0.84	Intermediate Similarity	NPC126284
0.8395	Intermediate Similarity	NPC191376
0.8395	Intermediate Similarity	NPC321505
0.8395	Intermediate Similarity	NPC179825
0.838	Intermediate Similarity	NPC206900
0.8373	Intermediate Similarity	NPC189266
0.8373	Intermediate Similarity	NPC2413
0.8373	Intermediate Similarity	NPC127674
0.8373	Intermediate Similarity	NPC204828
0.8373	Intermediate Similarity	NPC295691
0.8373	Intermediate Similarity	NPC276588
0.8373	Intermediate Similarity	NPC207757
0.8373	Intermediate Similarity	NPC278799
0.8373	Intermediate Similarity	NPC193949
0.8373	Intermediate Similarity	NPC249797
0.8373	Intermediate Similarity	NPC469817
0.8373	Intermediate Similarity	NPC5238
0.8373	Intermediate Similarity	NPC110416
0.8373	Intermediate Similarity	NPC184026
0.8373	Intermediate Similarity	NPC39701
0.8373	Intermediate Similarity	NPC172765
0.8373	Intermediate Similarity	NPC54379
0.8371	Intermediate Similarity	NPC65312
0.8371	Intermediate Similarity	NPC139783
0.8363	Intermediate Similarity	NPC247389
0.8362	Intermediate Similarity	NPC274716
0.8362	Intermediate Similarity	NPC167116
0.8362	Intermediate Similarity	NPC254441
0.8362	Intermediate Similarity	NPC302275
0.8353	Intermediate Similarity	NPC167546
0.8353	Intermediate Similarity	NPC302527
0.8353	Intermediate Similarity	NPC16805
0.8352	Intermediate Similarity	NPC257269
0.8351	Intermediate Similarity	NPC46990

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 NPC148709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	772
0.2-0.3	1145
0.3-0.4	2111
0.4-0.5	2646
0.5-0.6	1552
0.6-0.7	583
0.7-0.8	125
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
0.8409	Intermediate Similarity	NPD8054	Approved
0.8409	Intermediate Similarity	NPD8053	Approved
0.8333	Intermediate Similarity	NPD2421	Approved
0.8333	Intermediate Similarity	NPD2420	Approved
0.8295	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD3845	Phase 1
0.8103	Intermediate Similarity	NPD2489	Approved
0.8103	Intermediate Similarity	NPD27	Approved
0.8092	Intermediate Similarity	NPD3051	Approved
0.8066	Intermediate Similarity	NPD7906	Approved
0.8046	Intermediate Similarity	NPD2970	Approved
0.8046	Intermediate Similarity	NPD2969	Approved
0.8045	Intermediate Similarity	NPD4578	Approved
0.8045	Intermediate Similarity	NPD4577	Approved
0.8012	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6788	Approved
0.8011	Intermediate Similarity	NPD8251	Approved
0.8011	Intermediate Similarity	NPD8099	Discontinued
0.8011	Intermediate Similarity	NPD8252	Approved
0.7966	Intermediate Similarity	NPD8156	Discontinued
0.7952	Intermediate Similarity	NPD4584	Approved
0.7952	Intermediate Similarity	NPD1424	Approved
0.7914	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD4663	Approved
0.7845	Intermediate Similarity	NPD7310	Approved
0.7845	Intermediate Similarity	NPD7312	Approved
0.7845	Intermediate Similarity	NPD7311	Approved
0.7845	Intermediate Similarity	NPD7313	Approved
0.7836	Intermediate Similarity	NPD7298	Approved
0.7802	Intermediate Similarity	NPD7309	Approved
0.7797	Intermediate Similarity	NPD2898	Approved
0.7751	Intermediate Similarity	NPD6030	Approved
0.7751	Intermediate Similarity	NPD6031	Approved
0.7688	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5241	Discontinued
0.7657	Intermediate Similarity	NPD4055	Discovery
0.7594	Intermediate Similarity	NPD2490	Approved
0.7594	Intermediate Similarity	NPD2488	Approved
0.7584	Intermediate Similarity	NPD4010	Discontinued
0.7576	Intermediate Similarity	NPD7827	Phase 1
0.7558	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7833	Phase 2
0.7557	Intermediate Similarity	NPD7831	Phase 2
0.7545	Intermediate Similarity	NPD3060	Approved
0.7513	Intermediate Similarity	NPD3452	Approved
0.7513	Intermediate Similarity	NPD3450	Approved
0.7513	Intermediate Similarity	NPD2494	Approved
0.7513	Intermediate Similarity	NPD2493	Approved
0.75	Intermediate Similarity	NPD4481	Phase 3
0.7486	Intermediate Similarity	NPD6071	Discontinued
0.7486	Intermediate Similarity	NPD2978	Approved
0.7486	Intermediate Similarity	NPD4585	Approved
0.7486	Intermediate Similarity	NPD2977	Approved
0.7459	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4017	Approved
0.7443	Intermediate Similarity	NPD2560	Approved
0.7443	Intermediate Similarity	NPD2563	Approved
0.7427	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4583	Approved
0.7398	Intermediate Similarity	NPD4582	Approved
0.7391	Intermediate Similarity	NPD6297	Approved
0.7377	Intermediate Similarity	NPD42	Phase 2
0.7377	Intermediate Similarity	NPD6042	Phase 2
0.7374	Intermediate Similarity	NPD4666	Phase 3
0.7371	Intermediate Similarity	NPD4772	Phase 2
0.7371	Intermediate Similarity	NPD4773	Phase 2
0.7356	Intermediate Similarity	NPD4005	Discontinued
0.7353	Intermediate Similarity	NPD5160	Discontinued
0.7353	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4004	Approved
0.7347	Intermediate Similarity	NPD4002	Approved
0.7341	Intermediate Similarity	NPD5976	Discontinued
0.7326	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5709	Phase 3
0.731	Intermediate Similarity	NPD4040	Phase 1
0.7306	Intermediate Similarity	NPD2973	Approved
0.7306	Intermediate Similarity	NPD2975	Approved
0.7306	Intermediate Similarity	NPD2974	Approved
0.7283	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2968	Approved
0.7273	Intermediate Similarity	NPD3109	Approved
0.7273	Intermediate Similarity	NPD2971	Approved
0.7273	Intermediate Similarity	NPD3110	Approved
0.7267	Intermediate Similarity	NPD3053	Approved
0.7267	Intermediate Similarity	NPD7598	Phase 2
0.7267	Intermediate Similarity	NPD3055	Approved
0.7264	Intermediate Similarity	NPD6723	Discontinued
0.7243	Intermediate Similarity	NPD7479	Phase 2
0.7241	Intermediate Similarity	NPD3639	Approved
0.7241	Intermediate Similarity	NPD3641	Approved
0.7241	Intermediate Similarity	NPD4727	Phase 1
0.7241	Intermediate Similarity	NPD3640	Phase 3
0.7235	Intermediate Similarity	NPD5177	Phase 3
0.7234	Intermediate Similarity	NPD6851	Approved
0.7234	Intermediate Similarity	NPD6853	Approved
0.7231	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8095	Phase 1
0.7209	Intermediate Similarity	NPD7124	Phase 2
0.7206	Intermediate Similarity	NPD7047	Phase 3
0.7202	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4580	Approved
0.7189	Intermediate Similarity	NPD4873	Discontinued
0.7186	Intermediate Similarity	NPD817	Approved
0.7186	Intermediate Similarity	NPD823	Approved
0.7184	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4256	Phase 2
0.7176	Intermediate Similarity	NPD4257	Approved
0.7165	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6997	Phase 2
0.7152	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6107	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4162	Approved
0.7126	Intermediate Similarity	NPD7447	Phase 1
0.7112	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2674	Phase 3
0.7105	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4166	Phase 2
0.7093	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5156	Approved
0.7091	Intermediate Similarity	NPD5155	Approved
0.7083	Intermediate Similarity	NPD2568	Approved
0.7081	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6072	Discontinued
0.7069	Intermediate Similarity	NPD7213	Phase 3
0.7069	Intermediate Similarity	NPD7212	Phase 2
0.7052	Intermediate Similarity	NPD2677	Approved
0.7052	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5718	Phase 2
0.7037	Intermediate Similarity	NPD7549	Discontinued
0.7035	Intermediate Similarity	NPD3515	Approved
0.7035	Intermediate Similarity	NPD3516	Approved
0.703	Intermediate Similarity	NPD2606	Approved
0.703	Intermediate Similarity	NPD3595	Approved
0.703	Intermediate Similarity	NPD2605	Approved
0.703	Intermediate Similarity	NPD3594	Approved
0.7023	Intermediate Similarity	NPD7922	Phase 1
0.7022	Intermediate Similarity	NPD4675	Approved
0.7022	Intermediate Similarity	NPD4678	Approved
0.7018	Intermediate Similarity	NPD4726	Approved
0.7018	Intermediate Similarity	NPD4721	Approved
0.7018	Intermediate Similarity	NPD4725	Approved
0.7006	Intermediate Similarity	NPD1130	Approved
0.7006	Intermediate Similarity	NPD1136	Approved
0.7006	Intermediate Similarity	NPD1132	Approved
0.7	Intermediate Similarity	NPD2155	Approved
0.7	Intermediate Similarity	NPD1753	Discontinued
0.7	Intermediate Similarity	NPD2156	Approved
0.7	Intermediate Similarity	NPD2154	Approved
0.6995	Remote Similarity	NPD5677	Discontinued
0.6994	Remote Similarity	NPD5310	Approved
0.6994	Remote Similarity	NPD5311	Approved
0.6988	Remote Similarity	NPD4625	Phase 3
0.6988	Remote Similarity	NPD3027	Phase 3
0.6988	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5089	Approved
0.6983	Remote Similarity	NPD5090	Approved
0.6978	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4083	Discontinued
0.697	Remote Similarity	NPD3637	Approved
0.697	Remote Similarity	NPD3636	Approved
0.697	Remote Similarity	NPD3635	Approved
0.6966	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3059	Approved
0.6964	Remote Similarity	NPD3062	Approved
0.6964	Remote Similarity	NPD3061	Approved
0.6957	Remote Similarity	NPD7802	Discontinued
0.6952	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3448	Approved
0.695	Remote Similarity	NPD5006	Approved
0.695	Remote Similarity	NPD5005	Approved
0.695	Remote Similarity	NPD2491	Approved
0.695	Remote Similarity	NPD3057	Approved
0.6946	Remote Similarity	NPD598	Approved
0.6946	Remote Similarity	NPD601	Approved
0.6946	Remote Similarity	NPD3145	Approved
0.6946	Remote Similarity	NPD3144	Approved
0.6946	Remote Similarity	NPD597	Approved
0.6944	Remote Similarity	NPD3383	Approved
0.6944	Remote Similarity	NPD3384	Approved
0.6944	Remote Similarity	NPD3382	Approved
0.6935	Remote Similarity	NPD6612	Phase 2
0.6932	Remote Similarity	NPD3645	Discontinued
0.6928	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.692	Remote Similarity	NPD8152	Approved
0.692	Remote Similarity	NPD8153	Approved
0.6919	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4474	Approved
0.6905	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4475	Approved
0.6893	Remote Similarity	NPD6090	Discontinued
0.6882	Remote Similarity	NPD3052	Approved
0.6882	Remote Similarity	NPD5314	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