NPASS Compound

Structure

NPC192939 OpenBabel07101718302D 22 25 0 0 0 0 0 0 0 0999 V2000 1.4933 4.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2306 3.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0971 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7888 2.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5543 2.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 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 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6843 3.8473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2666 3.2803 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 8 1 0 0 0 0 5 12 2 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.08
Volume:	293.428
LogP:	3.673
LogD:	2.865
LogS:	-6.183
# Rotatable Bonds:	2
TPSA:	67.79
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	2.595
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.997
MDCK Permeability:	1.2887804587080609e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.616
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	91.70645141601562%
Volume Distribution (VD):	0.675
Pgp-substrate:	9.528931617736816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.576
CYP2D6-substrate:	0.434
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	3.629
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.692
Skin Sensitization:	0.889
Carcinogencity:	0.38
Eye Corrosion:	0.006
Eye Irritation:	0.816
Respiratory Toxicity:	0.701

Download Data

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

Natural Product: NPC192939

Natural Product ID:	NPC192939
*Common Name:**	Velutinam
IUPAC Name:	n.a.
Synonyms:	Velutinam
Standard InCHIKey:	KUZNZVMKXPBYIB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H13NO4/c1-21-13-7-10-14-11(18-17(10)20)6-9-8(4-3-5-12(9)19)15(14)16(13)22-2/h3-7,19H,1-2H3,(H,18,20)
SMILES:	COc1c(OC)cc2c3c1c1cccc(c1cc3N=C2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519045
PubChem CID:	9994639
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	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	6

Activity Type	# Activity
CELL-LINE	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	92.1	%	PMID[549740]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	37.5	%	PMID[549740]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	18.4	%	PMID[549740]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	87.3	%	PMID[549740]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	77.5	%	PMID[549740]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	65.4	%	PMID[549740]

☑ 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 NPC192939 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	501
0.1-0.2	2235
0.2-0.3	9621
0.3-0.4	7792
0.4-0.5	6446
0.5-0.6	12527
0.6-0.7	3136
0.7-0.8	404
0.8-0.85	15
0.85-0.9	1
0.9-0.95	7
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215747
0.9938	High Similarity	NPC260118
0.9878	High Similarity	NPC28425
0.9877	High Similarity	NPC265383
0.9817	High Similarity	NPC119579
0.9756	High Similarity	NPC311936
0.9641	High Similarity	NPC219170
0.9641	High Similarity	NPC180253
0.9527	High Similarity	NPC112676
0.9527	High Similarity	NPC296742
0.9521	High Similarity	NPC276060
0.9467	High Similarity	NPC224293
0.9467	High Similarity	NPC22928
0.9408	High Similarity	NPC69213
0.9302	High Similarity	NPC294244
0.9195	High Similarity	NPC29472
0.8791	High Similarity	NPC159101
0.838	Intermediate Similarity	NPC320088
0.8284	Intermediate Similarity	NPC235628
0.8268	Intermediate Similarity	NPC33902
0.8268	Intermediate Similarity	NPC276674
0.8263	Intermediate Similarity	NPC18614
0.8249	Intermediate Similarity	NPC190461
0.8204	Intermediate Similarity	NPC52475
0.8197	Intermediate Similarity	NPC78284
0.8079	Intermediate Similarity	NPC285941
0.8033	Intermediate Similarity	NPC474904
0.8033	Intermediate Similarity	NPC312531
0.8023	Intermediate Similarity	NPC231371
0.8023	Intermediate Similarity	NPC168153
0.8	Intermediate Similarity	NPC68328
0.7912	Intermediate Similarity	NPC249405
0.7853	Intermediate Similarity	NPC474931
0.7853	Intermediate Similarity	NPC145832
0.7853	Intermediate Similarity	NPC306555
0.7853	Intermediate Similarity	NPC12053
0.7853	Intermediate Similarity	NPC81218
0.7853	Intermediate Similarity	NPC158376
0.7853	Intermediate Similarity	NPC117188
0.7853	Intermediate Similarity	NPC205421
0.7795	Intermediate Similarity	NPC121510
0.7795	Intermediate Similarity	NPC171882
0.7795	Intermediate Similarity	NPC85661
0.7765	Intermediate Similarity	NPC77359
0.7744	Intermediate Similarity	NPC46679
0.774	Intermediate Similarity	NPC477563
0.774	Intermediate Similarity	NPC78222
0.774	Intermediate Similarity	NPC13504
0.774	Intermediate Similarity	NPC306843
0.774	Intermediate Similarity	NPC136508
0.774	Intermediate Similarity	NPC212794
0.774	Intermediate Similarity	NPC96603
0.774	Intermediate Similarity	NPC253043
0.774	Intermediate Similarity	NPC196447
0.7733	Intermediate Similarity	NPC275027
0.7725	Intermediate Similarity	NPC162653
0.7688	Intermediate Similarity	NPC10875
0.7688	Intermediate Similarity	NPC10730
0.7684	Intermediate Similarity	NPC1229
0.7684	Intermediate Similarity	NPC324144
0.768	Intermediate Similarity	NPC477020
0.768	Intermediate Similarity	NPC192135
0.768	Intermediate Similarity	NPC66341
0.7677	Intermediate Similarity	NPC91234
0.7663	Intermediate Similarity	NPC179704
0.7659	Intermediate Similarity	NPC200888
0.7657	Intermediate Similarity	NPC476572
0.7653	Intermediate Similarity	NPC90185
0.765	Intermediate Similarity	NPC114364
0.765	Intermediate Similarity	NPC320223
0.7647	Intermediate Similarity	NPC16436
0.7627	Intermediate Similarity	NPC60186
0.7596	Intermediate Similarity	NPC287588
0.759	Intermediate Similarity	NPC38961
0.7582	Intermediate Similarity	NPC228040
0.7582	Intermediate Similarity	NPC474051
0.7571	Intermediate Similarity	NPC166014
0.7571	Intermediate Similarity	NPC27410
0.7569	Intermediate Similarity	NPC69712
0.7569	Intermediate Similarity	NPC477562
0.7569	Intermediate Similarity	NPC26240
0.7563	Intermediate Similarity	NPC100573
0.7563	Intermediate Similarity	NPC207873
0.7562	Intermediate Similarity	NPC240684
0.7557	Intermediate Similarity	NPC195766
0.7557	Intermediate Similarity	NPC206736
0.7552	Intermediate Similarity	NPC17677
0.7543	Intermediate Similarity	NPC99659
0.7543	Intermediate Similarity	NPC325871
0.7541	Intermediate Similarity	NPC128560
0.7541	Intermediate Similarity	NPC229166
0.7541	Intermediate Similarity	NPC199465
0.7527	Intermediate Similarity	NPC239775
0.7514	Intermediate Similarity	NPC329837
0.7512	Intermediate Similarity	NPC290227
0.7487	Intermediate Similarity	NPC135772
0.7486	Intermediate Similarity	NPC19555
0.7474	Intermediate Similarity	NPC25897
0.7473	Intermediate Similarity	NPC118274
0.7473	Intermediate Similarity	NPC168753
0.7462	Intermediate Similarity	NPC261388
0.7459	Intermediate Similarity	NPC247389
0.7459	Intermediate Similarity	NPC298979
0.7446	Intermediate Similarity	NPC477558
0.7435	Intermediate Similarity	NPC302001
0.7433	Intermediate Similarity	NPC248642
0.7427	Intermediate Similarity	NPC122463
0.7419	Intermediate Similarity	NPC474507
0.7411	Intermediate Similarity	NPC156728
0.7411	Intermediate Similarity	NPC244606
0.7403	Intermediate Similarity	NPC476573
0.7403	Intermediate Similarity	NPC219341
0.7403	Intermediate Similarity	NPC35627
0.7403	Intermediate Similarity	NPC476432
0.7403	Intermediate Similarity	NPC24264
0.7403	Intermediate Similarity	NPC81247
0.7401	Intermediate Similarity	NPC291359
0.7396	Intermediate Similarity	NPC470090
0.7394	Intermediate Similarity	NPC228843
0.7394	Intermediate Similarity	NPC156576
0.7381	Intermediate Similarity	NPC266006
0.738	Intermediate Similarity	NPC477561
0.738	Intermediate Similarity	NPC312918
0.738	Intermediate Similarity	NPC155442
0.738	Intermediate Similarity	NPC476574
0.7374	Intermediate Similarity	NPC304183
0.7371	Intermediate Similarity	NPC326316
0.7371	Intermediate Similarity	NPC81733
0.7363	Intermediate Similarity	NPC61731
0.7363	Intermediate Similarity	NPC150879
0.7363	Intermediate Similarity	NPC186569
0.7348	Intermediate Similarity	NPC167546
0.7348	Intermediate Similarity	NPC302527
0.7348	Intermediate Similarity	NPC16805
0.7348	Intermediate Similarity	NPC225774
0.7347	Intermediate Similarity	NPC471489
0.7345	Intermediate Similarity	NPC244112
0.7343	Intermediate Similarity	NPC118121
0.734	Intermediate Similarity	NPC298449
0.734	Intermediate Similarity	NPC116284
0.7337	Intermediate Similarity	NPC218131
0.7337	Intermediate Similarity	NPC105847
0.7337	Intermediate Similarity	NPC243759
0.7333	Intermediate Similarity	NPC212163
0.733	Intermediate Similarity	NPC26601
0.7326	Intermediate Similarity	NPC126284
0.7326	Intermediate Similarity	NPC5462
0.7317	Intermediate Similarity	NPC204446
0.7316	Intermediate Similarity	NPC57036
0.7312	Intermediate Similarity	NPC148709
0.7312	Intermediate Similarity	NPC476577
0.7312	Intermediate Similarity	NPC173416
0.7308	Intermediate Similarity	NPC257354
0.7294	Intermediate Similarity	NPC308768
0.7294	Intermediate Similarity	NPC12668
0.7292	Intermediate Similarity	NPC79213
0.7291	Intermediate Similarity	NPC124658
0.7291	Intermediate Similarity	NPC227361
0.7283	Intermediate Similarity	NPC152212
0.7278	Intermediate Similarity	NPC151656
0.7278	Intermediate Similarity	NPC230919
0.7278	Intermediate Similarity	NPC200935
0.7278	Intermediate Similarity	NPC266453
0.7268	Intermediate Similarity	NPC310894
0.7268	Intermediate Similarity	NPC210918
0.7259	Intermediate Similarity	NPC295676
0.7257	Intermediate Similarity	NPC211296
0.7253	Intermediate Similarity	NPC169743
0.7253	Intermediate Similarity	NPC134858
0.725	Intermediate Similarity	NPC193777
0.7249	Intermediate Similarity	NPC313886
0.7246	Intermediate Similarity	NPC174049
0.7238	Intermediate Similarity	NPC79402
0.7238	Intermediate Similarity	NPC24954
0.7238	Intermediate Similarity	NPC80759
0.7238	Intermediate Similarity	NPC204179
0.7235	Intermediate Similarity	NPC243996
0.7235	Intermediate Similarity	NPC132804
0.7235	Intermediate Similarity	NPC275061
0.7235	Intermediate Similarity	NPC220344
0.7225	Intermediate Similarity	NPC477186
0.7216	Intermediate Similarity	NPC184161
0.7216	Intermediate Similarity	NPC265473
0.7216	Intermediate Similarity	NPC219383
0.7216	Intermediate Similarity	NPC276665
0.7213	Intermediate Similarity	NPC90984
0.7209	Intermediate Similarity	NPC175838
0.7207	Intermediate Similarity	NPC186063
0.7207	Intermediate Similarity	NPC170503
0.7207	Intermediate Similarity	NPC203784
0.7207	Intermediate Similarity	NPC126519
0.7202	Intermediate Similarity	NPC114335
0.7202	Intermediate Similarity	NPC141915
0.7202	Intermediate Similarity	NPC280964
0.7198	Intermediate Similarity	NPC233650
0.7194	Intermediate Similarity	NPC193906
0.7194	Intermediate Similarity	NPC23080
0.7189	Intermediate Similarity	NPC6152
0.7188	Intermediate Similarity	NPC186546
0.7188	Intermediate Similarity	NPC476576

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 NPC192939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	792
0.2-0.3	950
0.3-0.4	1946
0.4-0.5	2602
0.5-0.6	1997
0.6-0.7	504
0.7-0.8	30
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
0.7733	Intermediate Similarity	NPD5617	Suspended
0.7569	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2883	Discontinued
0.7471	Intermediate Similarity	NPD5811	Approved
0.7459	Intermediate Similarity	NPD4083	Discontinued
0.7389	Intermediate Similarity	NPD1850	Phase 3
0.7386	Intermediate Similarity	NPD3778	Approved
0.736	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3453	Discontinued
0.7277	Intermediate Similarity	NPD2845	Phase 2
0.7277	Intermediate Similarity	NPD2843	Phase 2
0.7258	Intermediate Similarity	NPD3920	Phase 2
0.7232	Intermediate Similarity	NPD3296	Phase 1
0.7219	Intermediate Similarity	NPD6184	Discontinued
0.7219	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2789	Approved
0.7182	Intermediate Similarity	NPD4055	Discovery
0.7175	Intermediate Similarity	NPD4005	Discontinued
0.7151	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5641	Discontinued
0.7143	Intermediate Similarity	NPD4123	Phase 3
0.7135	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4951	Discontinued
0.7074	Intermediate Similarity	NPD7479	Phase 2
0.7072	Intermediate Similarity	NPD5599	Discontinued
0.7065	Intermediate Similarity	NPD2821	Approved
0.7043	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3763	Approved
0.7027	Intermediate Similarity	NPD3051	Approved
0.7024	Intermediate Similarity	NPD2674	Phase 3
0.7022	Intermediate Similarity	NPD4003	Phase 3
0.7021	Intermediate Similarity	NPD5810	Discontinued
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3236	Phase 3
0.6989	Remote Similarity	NPD2969	Approved
0.6989	Remote Similarity	NPD2970	Approved
0.6974	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7034	Discontinued
0.6959	Remote Similarity	NPD7906	Approved
0.6959	Remote Similarity	NPD3398	Discontinued
0.6952	Remote Similarity	NPD2489	Approved
0.6952	Remote Similarity	NPD27	Approved
0.6947	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4678	Approved
0.6944	Remote Similarity	NPD4675	Approved
0.6939	Remote Similarity	NPD3921	Approved
0.6939	Remote Similarity	NPD3922	Approved
0.6939	Remote Similarity	NPD3924	Approved
0.6939	Remote Similarity	NPD3923	Approved
0.6914	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6331	Phase 2
0.6904	Remote Similarity	NPD7262	Phase 1
0.6901	Remote Similarity	NPD4097	Suspended
0.6897	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2420	Approved
0.6893	Remote Similarity	NPD2421	Approved
0.6882	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6494	Phase 2
0.6881	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5241	Discontinued
0.6875	Remote Similarity	NPD3301	Approved
0.6872	Remote Similarity	NPD3349	Phase 2
0.6872	Remote Similarity	NPD5800	Discontinued
0.6866	Remote Similarity	NPD6612	Phase 2
0.6864	Remote Similarity	NPD3145	Approved
0.6864	Remote Similarity	NPD3144	Approved
0.6863	Remote Similarity	NPD5530	Phase 1
0.6854	Remote Similarity	NPD4584	Approved
0.6853	Remote Similarity	NPD3963	Phase 1
0.6839	Remote Similarity	NPD4577	Approved
0.6839	Remote Similarity	NPD7311	Approved
0.6839	Remote Similarity	NPD7310	Approved
0.6839	Remote Similarity	NPD4578	Approved
0.6839	Remote Similarity	NPD7312	Approved
0.6839	Remote Similarity	NPD7313	Approved
0.6831	Remote Similarity	NPD5929	Approved
0.6829	Remote Similarity	NPD7263	Phase 2
0.6821	Remote Similarity	NPD4663	Approved
0.6818	Remote Similarity	NPD7125	Discontinued
0.6813	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7831	Phase 2
0.6811	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7833	Phase 2
0.6804	Remote Similarity	NPD8053	Approved
0.6804	Remote Similarity	NPD7309	Approved
0.6804	Remote Similarity	NPD8054	Approved
0.68	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6527	Approved
0.6798	Remote Similarity	NPD4357	Discontinued
0.6789	Remote Similarity	NPD8067	Phase 3
0.6784	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2161	Phase 2
0.6779	Remote Similarity	NPD4502	Phase 2
0.6777	Remote Similarity	NPD5164	Discontinued
0.6757	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7546	Discontinued
0.6747	Remote Similarity	NPD1669	Approved
0.6743	Remote Similarity	NPD1375	Discontinued
0.6739	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6037	Discontinued
0.6723	Remote Similarity	NPD5819	Phase 2
0.672	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3515	Approved
0.6716	Remote Similarity	NPD3516	Approved
0.6716	Remote Similarity	NPD4604	Approved
0.6716	Remote Similarity	NPD4605	Approved
0.6704	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3556	Approved
0.6703	Remote Similarity	NPD2563	Approved
0.6703	Remote Similarity	NPD2560	Approved
0.6703	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3560	Approved
0.6703	Remote Similarity	NPD3557	Approved
0.6703	Remote Similarity	NPD3558	Approved
0.6686	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6031	Approved
0.6685	Remote Similarity	NPD6030	Approved
0.6684	Remote Similarity	NPD4481	Phase 3
0.6684	Remote Similarity	NPD6339	Approved
0.6684	Remote Similarity	NPD2898	Approved
0.6684	Remote Similarity	NPD6340	Approved
0.6667	Remote Similarity	NPD3342	Phase 2
0.6667	Remote Similarity	NPD3815	Phase 1
0.6667	Remote Similarity	NPD5109	Approved
0.6667	Remote Similarity	NPD5582	Discontinued
0.6667	Remote Similarity	NPD5110	Phase 2
0.6667	Remote Similarity	NPD3816	Phase 1
0.6667	Remote Similarity	NPD5111	Phase 2
0.6667	Remote Similarity	NPD7773	Phase 2
0.6651	Remote Similarity	NPD8149	Discontinued
0.665	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6526	Approved
0.6631	Remote Similarity	NPD5604	Discontinued
0.663	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7477	Discontinued
0.6617	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8099	Discontinued
0.6615	Remote Similarity	NPD8252	Approved
0.6615	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8251	Approved
0.6613	Remote Similarity	NPD6063	Approved
0.6612	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1558	Phase 1
0.6587	Remote Similarity	NPD7222	Phase 2
0.6587	Remote Similarity	NPD7453	Approved
0.6587	Remote Similarity	NPD5429	Discontinued
0.6587	Remote Similarity	NPD7452	Approved
0.6584	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.658	Remote Similarity	NPD8156	Discontinued
0.6579	Remote Similarity	NPD6071	Discontinued
0.6577	Remote Similarity	NPD7922	Phase 1
0.6576	Remote Similarity	NPD6502	Phase 2
0.6561	Remote Similarity	NPD6746	Phase 2
0.6559	Remote Similarity	NPD5773	Approved
0.6559	Remote Similarity	NPD5772	Approved
0.6557	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5658	Approved
0.6555	Remote Similarity	NPD4859	Phase 1
0.6554	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2488	Approved
0.655	Remote Similarity	NPD2490	Approved
0.6546	Remote Similarity	NPD5557	Phase 1
0.6545	Remote Similarity	NPD2216	Approved
0.6545	Remote Similarity	NPD2215	Approved
0.6541	Remote Similarity	NPD5089	Approved
0.6541	Remote Similarity	NPD5090	Approved
0.654	Remote Similarity	NPD5936	Approved
0.654	Remote Similarity	NPD5939	Approved
0.6538	Remote Similarity	NPD6090	Discontinued
0.6538	Remote Similarity	NPD4319	Phase 2
0.6536	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1898	Discontinued
0.6528	Remote Similarity	NPD3909	Discontinued
0.6528	Remote Similarity	NPD5930	Phase 3
0.6517	Remote Similarity	NPD3634	Approved
0.6517	Remote Similarity	NPD7153	Discontinued
0.6517	Remote Similarity	NPD3633	Approved
0.6509	Remote Similarity	NPD7225	Discontinued
0.6509	Remote Similarity	NPD2922	Phase 1
0.6505	Remote Similarity	NPD3452	Approved
0.6505	Remote Similarity	NPD2494	Approved
0.6505	Remote Similarity	NPD3450	Approved
0.6505	Remote Similarity	NPD2493	Approved
0.6502	Remote Similarity	NPD6723	Discontinued
0.65	Remote Similarity	NPD3692	Discontinued
0.65	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5895	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