NPASS Compound

Structure

NPC291359 OpenBabel07101718192D 26 28 0 0 1 0 0 0 0 0999 V2000 -5.0170 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8531 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5344 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0516 0.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0516 1.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0861 0.1294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0861 1.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6034 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 1.4483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 0.9655 0.0000 C 0 0 2 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 -3.3446 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1551 1.8017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 2.4138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 6 0 0 0 19 26 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.16
Volume:	371.169
LogP:	3.834
LogD:	3.008
LogS:	-4.149
# Rotatable Bonds:	4
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	3.604
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.687
MDCK Permeability:	1.5530928067164496e-05
Pgp-inhibitor:	0.361
Pgp-substrate:	0.621
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	96.0682144165039%
Volume Distribution (VD):	0.897
Pgp-substrate:	3.524778127670288%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.333
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.361
CYP2C9-substrate:	0.619
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	5.844
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.455
Rat Oral Acute Toxicity:	0.287
Maximum Recommended Daily Dose:	0.117
Skin Sensitization:	0.757
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.364

Download Data

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

Natural Product: NPC291359

Natural Product ID:	NPC291359
*Common Name:**	Aniduquinolone C
IUPAC Name:	(3S,4S)-4,5-dihydroxy-3-methoxy-6-(3-methylbut-2-enyl)-4-phenyl-1,3-dihydroquinolin-2-one
Synonyms:
Standard InCHIKey:	DRIVJEVMJVKUHC-CTNGQTDRSA-N
Standard InCHI:	InChI=1S/C21H23NO4/c1-13(2)9-10-14-11-12-16-17(18(14)23)21(25,15-7-5-4-6-8-15)19(26-3)20(24)22-16/h4-9,11-12,19,23,25H,10H2,1-3H3,(H,22,24)/t19-,21+/m1/s1
SMILES:	CO[C@@H]1C(=Nc2c([C@@]1(O)c1ccccc1)c(O)c(cc2)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431782
PubChem CID:	72703462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO32457	Aspergillus nidulans	Under-species	n.a.	n.a.	n.a.	isolated from the mangrove plant Rhizophora stylosa.	n.a.	PMID[24099304]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	4.5	uM	PMID[518763]

☑ 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 NPC291359 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	275
0.1-0.2	1281
0.2-0.3	6308
0.3-0.4	11307
0.4-0.5	9826
0.5-0.6	12404
0.6-0.7	1238
0.7-0.8	43
0.8-0.85	6
0.85-0.9	1
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC19555
0.9542	High Similarity	NPC257354
0.9524	High Similarity	NPC184161
0.9299	High Similarity	NPC168153
0.9182	High Similarity	NPC472331
0.9182	High Similarity	NPC126515
0.9182	High Similarity	NPC274002
0.8354	Intermediate Similarity	NPC10730
0.8354	Intermediate Similarity	NPC10875
0.8202	Intermediate Similarity	NPC472329
0.8202	Intermediate Similarity	NPC472330
0.8095	Intermediate Similarity	NPC197680
0.8095	Intermediate Similarity	NPC259098
0.7716	Intermediate Similarity	NPC219383
0.7564	Intermediate Similarity	NPC166667
0.75	Intermediate Similarity	NPC225381
0.7486	Intermediate Similarity	NPC22928
0.743	Intermediate Similarity	NPC219170
0.743	Intermediate Similarity	NPC180253
0.7417	Intermediate Similarity	NPC325013
0.7416	Intermediate Similarity	NPC28425
0.7416	Intermediate Similarity	NPC276060
0.7401	Intermediate Similarity	NPC192939
0.7401	Intermediate Similarity	NPC311936
0.7401	Intermediate Similarity	NPC215747
0.736	Intermediate Similarity	NPC119579
0.7345	Intermediate Similarity	NPC260118
0.7294	Intermediate Similarity	NPC72291
0.7288	Intermediate Similarity	NPC265383
0.7216	Intermediate Similarity	NPC231371
0.7174	Intermediate Similarity	NPC294244
0.7135	Intermediate Similarity	NPC235628
0.7125	Intermediate Similarity	NPC126637
0.7099	Intermediate Similarity	NPC314113
0.7086	Intermediate Similarity	NPC68328
0.7065	Intermediate Similarity	NPC112676
0.7065	Intermediate Similarity	NPC296742
0.7045	Intermediate Similarity	NPC310894
0.7011	Intermediate Similarity	NPC224293
0.7005	Intermediate Similarity	NPC29472
0.6979	Remote Similarity	NPC159101
0.6957	Remote Similarity	NPC69213
0.6935	Remote Similarity	NPC28510
0.6907	Remote Similarity	NPC476106
0.6901	Remote Similarity	NPC275027
0.6889	Remote Similarity	NPC9475
0.6885	Remote Similarity	NPC190007
0.6871	Remote Similarity	NPC9336
0.6862	Remote Similarity	NPC79293
0.6862	Remote Similarity	NPC279401
0.6853	Remote Similarity	NPC25961
0.6848	Remote Similarity	NPC94943
0.6839	Remote Similarity	NPC306366
0.6839	Remote Similarity	NPC156348
0.6828	Remote Similarity	NPC320088
0.6818	Remote Similarity	NPC204179
0.6813	Remote Similarity	NPC313466
0.68	Remote Similarity	NPC329837
0.68	Remote Similarity	NPC205652
0.6796	Remote Similarity	NPC200888
0.6757	Remote Similarity	NPC313886
0.6754	Remote Similarity	NPC243834
0.6754	Remote Similarity	NPC70956
0.6753	Remote Similarity	NPC475112
0.6753	Remote Similarity	NPC475085
0.6753	Remote Similarity	NPC291535
0.6748	Remote Similarity	NPC64205
0.6743	Remote Similarity	NPC206736
0.6743	Remote Similarity	NPC195766
0.6739	Remote Similarity	NPC212535
0.6723	Remote Similarity	NPC15506
0.6721	Remote Similarity	NPC39822
0.672	Remote Similarity	NPC33902
0.672	Remote Similarity	NPC276674
0.6703	Remote Similarity	NPC477187
0.6703	Remote Similarity	NPC62069
0.67	Remote Similarity	NPC116178
0.6689	Remote Similarity	NPC473137
0.6689	Remote Similarity	NPC12656
0.6667	Remote Similarity	NPC153042
0.6667	Remote Similarity	NPC217903
0.6667	Remote Similarity	NPC316161
0.6647	Remote Similarity	NPC470090
0.6645	Remote Similarity	NPC223451
0.6631	Remote Similarity	NPC291759
0.663	Remote Similarity	NPC478032
0.6625	Remote Similarity	NPC101372
0.6625	Remote Similarity	NPC295478
0.6623	Remote Similarity	NPC474544
0.6623	Remote Similarity	NPC1986
0.6615	Remote Similarity	NPC232600
0.6613	Remote Similarity	NPC320394
0.6612	Remote Similarity	NPC283152
0.6612	Remote Similarity	NPC474051
0.6599	Remote Similarity	NPC137929
0.6599	Remote Similarity	NPC164374
0.6596	Remote Similarity	NPC66083
0.6593	Remote Similarity	NPC95412
0.6592	Remote Similarity	NPC238430
0.6584	Remote Similarity	NPC321166
0.658	Remote Similarity	NPC474188
0.6578	Remote Similarity	NPC133591
0.6575	Remote Similarity	NPC83241
0.6571	Remote Similarity	NPC477889
0.657	Remote Similarity	NPC476744
0.6566	Remote Similarity	NPC304183
0.6558	Remote Similarity	NPC311737
0.6558	Remote Similarity	NPC38458
0.6557	Remote Similarity	NPC288943
0.6546	Remote Similarity	NPC72211
0.6545	Remote Similarity	NPC114335
0.6545	Remote Similarity	NPC280964
0.6545	Remote Similarity	NPC141915
0.6543	Remote Similarity	NPC38823
0.6543	Remote Similarity	NPC207033
0.6538	Remote Similarity	NPC477185
0.6538	Remote Similarity	NPC474409
0.6535	Remote Similarity	NPC48353
0.6533	Remote Similarity	NPC193777
0.6524	Remote Similarity	NPC184437
0.6522	Remote Similarity	NPC477839
0.6522	Remote Similarity	NPC477532
0.6519	Remote Similarity	NPC471315
0.6519	Remote Similarity	NPC471314
0.6512	Remote Similarity	NPC476743
0.651	Remote Similarity	NPC78284
0.6505	Remote Similarity	NPC190461
0.6505	Remote Similarity	NPC475962
0.65	Remote Similarity	NPC278887
0.65	Remote Similarity	NPC470931
0.65	Remote Similarity	NPC278097
0.6494	Remote Similarity	NPC147957
0.6494	Remote Similarity	NPC82963
0.6491	Remote Similarity	NPC472100
0.649	Remote Similarity	NPC308689
0.6485	Remote Similarity	NPC92805
0.6485	Remote Similarity	NPC317872
0.6484	Remote Similarity	NPC158376
0.6484	Remote Similarity	NPC12053
0.6484	Remote Similarity	NPC117188
0.6484	Remote Similarity	NPC145832
0.6484	Remote Similarity	NPC306555
0.6484	Remote Similarity	NPC205421
0.6484	Remote Similarity	NPC474931
0.6484	Remote Similarity	NPC81218
0.648	Remote Similarity	NPC139506
0.648	Remote Similarity	NPC292143
0.6477	Remote Similarity	NPC477156
0.6477	Remote Similarity	NPC477157
0.6477	Remote Similarity	NPC205934
0.6477	Remote Similarity	NPC43787
0.6474	Remote Similarity	NPC246700
0.6474	Remote Similarity	NPC477186
0.6474	Remote Similarity	NPC295287
0.6471	Remote Similarity	NPC470550
0.6468	Remote Similarity	NPC168250
0.6467	Remote Similarity	NPC20829
0.6467	Remote Similarity	NPC18189
0.6467	Remote Similarity	NPC262585
0.6465	Remote Similarity	NPC162484
0.6457	Remote Similarity	NPC476741
0.645	Remote Similarity	NPC198160
0.6448	Remote Similarity	NPC182257
0.6446	Remote Similarity	NPC124085
0.6446	Remote Similarity	NPC117048
0.6443	Remote Similarity	NPC70259
0.6443	Remote Similarity	NPC303214
0.6443	Remote Similarity	NPC76327
0.6442	Remote Similarity	NPC329830
0.6441	Remote Similarity	NPC469428
0.6441	Remote Similarity	NPC70549
0.644	Remote Similarity	NPC474059
0.6436	Remote Similarity	NPC477392
0.6436	Remote Similarity	NPC315934
0.6433	Remote Similarity	NPC471598
0.6432	Remote Similarity	NPC289743
0.6432	Remote Similarity	NPC313112
0.6432	Remote Similarity	NPC110374
0.6432	Remote Similarity	NPC301292
0.6432	Remote Similarity	NPC133156
0.6432	Remote Similarity	NPC285941
0.6429	Remote Similarity	NPC477888
0.6429	Remote Similarity	NPC222982
0.6429	Remote Similarity	NPC90984
0.6429	Remote Similarity	NPC288430
0.6429	Remote Similarity	NPC37302
0.6425	Remote Similarity	NPC289776
0.6425	Remote Similarity	NPC57105
0.6425	Remote Similarity	NPC191863
0.6425	Remote Similarity	NPC133470
0.6424	Remote Similarity	NPC44732
0.6414	Remote Similarity	NPC474077
0.6414	Remote Similarity	NPC66815
0.6413	Remote Similarity	NPC118274
0.6413	Remote Similarity	NPC168753
0.6409	Remote Similarity	NPC324144
0.6409	Remote Similarity	NPC1229
0.6406	Remote Similarity	NPC475411
0.6406	Remote Similarity	NPC469390
0.6406	Remote Similarity	NPC70340

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 NPC291359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	635
0.2-0.3	883
0.3-0.4	1670
0.4-0.5	3125
0.5-0.6	2358
0.6-0.7	277
0.7-0.8	9
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
0.7622	Intermediate Similarity	NPD5617	Suspended
0.7341	Intermediate Similarity	NPD2215	Approved
0.7341	Intermediate Similarity	NPD2216	Approved
0.7333	Intermediate Similarity	NPD4951	Discontinued
0.7305	Intermediate Similarity	NPD3296	Phase 1
0.7297	Intermediate Similarity	NPD4605	Approved
0.7297	Intermediate Similarity	NPD4604	Approved
0.7262	Intermediate Similarity	NPD3778	Approved
0.7191	Intermediate Similarity	NPD6184	Discontinued
0.7052	Intermediate Similarity	NPD3453	Discontinued
0.6973	Remote Similarity	NPD2843	Phase 2
0.6973	Remote Similarity	NPD2845	Phase 2
0.6959	Remote Similarity	NPD2789	Approved
0.6898	Remote Similarity	NPD5937	Approved
0.6882	Remote Similarity	NPD4003	Phase 3
0.686	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5599	Discontinued
0.6839	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3793	Phase 3
0.6791	Remote Similarity	NPD7628	Phase 3
0.6791	Remote Similarity	NPD7630	Phase 3
0.6791	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3236	Phase 3
0.6763	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5811	Approved
0.6708	Remote Similarity	NPD2322	Discovery
0.6685	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6072	Discontinued
0.6649	Remote Similarity	NPD4771	Phase 2
0.6649	Remote Similarity	NPD7883	Discontinued
0.6648	Remote Similarity	NPD6063	Approved
0.6646	Remote Similarity	NPD6320	Approved
0.6632	Remote Similarity	NPD2727	Phase 2
0.6629	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1835	Phase 1
0.6616	Remote Similarity	NPD6296	Discontinued
0.6616	Remote Similarity	NPD7263	Phase 2
0.6615	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5984	Phase 2
0.6596	Remote Similarity	NPD3120	Approved
0.6596	Remote Similarity	NPD3119	Phase 1
0.6592	Remote Similarity	NPD1850	Phase 3
0.6592	Remote Similarity	NPD7129	Suspended
0.6591	Remote Similarity	NPD6283	Phase 2
0.6579	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1169	Approved
0.6564	Remote Similarity	NPD7477	Discontinued
0.6559	Remote Similarity	NPD4012	Approved
0.6522	Remote Similarity	NPD6159	Phase 2
0.6512	Remote Similarity	NPD681	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5150	Phase 2
0.6506	Remote Similarity	NPD3552	Approved
0.6506	Remote Similarity	NPD3555	Approved
0.6506	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3554	Approved
0.6506	Remote Similarity	NPD3553	Approved
0.65	Remote Similarity	NPD2579	Approved
0.6495	Remote Similarity	NPD5652	Approved
0.6495	Remote Similarity	NPD5651	Approved
0.6495	Remote Similarity	NPD5650	Approved
0.6486	Remote Similarity	NPD7479	Phase 2
0.6477	Remote Similarity	NPD2468	Approved
0.6477	Remote Similarity	NPD2469	Approved
0.6471	Remote Similarity	NPD6331	Phase 2
0.6463	Remote Similarity	NPD6405	Approved
0.6463	Remote Similarity	NPD6407	Approved
0.6461	Remote Similarity	NPD3557	Approved
0.6461	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3558	Approved
0.6461	Remote Similarity	NPD3560	Approved
0.6461	Remote Similarity	NPD3556	Approved
0.6458	Remote Similarity	NPD3601	Discontinued
0.6458	Remote Similarity	NPD3634	Approved
0.6458	Remote Similarity	NPD3633	Approved
0.6458	Remote Similarity	NPD3963	Phase 1
0.6455	Remote Similarity	NPD5565	Discontinued
0.6443	Remote Similarity	NPD9507	Approved
0.644	Remote Similarity	NPD3342	Phase 2
0.6432	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7125	Discontinued
0.6413	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2883	Discontinued
0.64	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4103	Phase 2
0.6393	Remote Similarity	NPD4083	Discontinued
0.6392	Remote Similarity	NPD4523	Approved
0.6389	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8070	Approved
0.6383	Remote Similarity	NPD2802	Phase 3
0.6374	Remote Similarity	NPD2821	Approved
0.6374	Remote Similarity	NPD3400	Discontinued
0.6373	Remote Similarity	NPD4740	Approved
0.6369	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2674	Phase 3
0.6364	Remote Similarity	NPD4005	Discontinued
0.6364	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2420	Approved
0.6358	Remote Similarity	NPD2421	Approved
0.6353	Remote Similarity	NPD1908	Phase 2
0.6349	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7262	Phase 1
0.6339	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD3516	Approved
0.6332	Remote Similarity	NPD3515	Approved
0.6331	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1413	Approved
0.6319	Remote Similarity	NPD1411	Approved
0.6319	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1414	Approved
0.6318	Remote Similarity	NPD3003	Approved
0.631	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD1339	Discontinued
0.6301	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4055	Discovery
0.6296	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2166	Phase 3
0.6294	Remote Similarity	NPD6789	Approved
0.6294	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5587	Approved
0.6284	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5819	Phase 2
0.6279	Remote Similarity	NPD8067	Phase 3
0.6277	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4931	Phase 2
0.627	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD840	Approved
0.6265	Remote Similarity	NPD1595	Approved
0.6265	Remote Similarity	NPD1594	Phase 3
0.6265	Remote Similarity	NPD839	Approved
0.6264	Remote Similarity	NPD1615	Approved
0.6264	Remote Similarity	NPD1543	Discontinued
0.6263	Remote Similarity	NPD6874	Approved
0.6263	Remote Similarity	NPD7546	Discontinued
0.6257	Remote Similarity	NPD75	Approved
0.6257	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD9277	Approved
0.625	Remote Similarity	NPD5164	Discontinued
0.625	Remote Similarity	NPD471	Approved
0.6244	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6527	Approved
0.6242	Remote Similarity	NPD4275	Approved
0.6242	Remote Similarity	NPD3720	Discontinued
0.6242	Remote Similarity	NPD4274	Approved
0.6237	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD5903	Approved
0.6232	Remote Similarity	NPD5902	Approved
0.623	Remote Similarity	NPD3251	Approved
0.6229	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD2238	Phase 2
0.6226	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3398	Discontinued
0.6216	Remote Similarity	NPD3975	Discontinued
0.6212	Remote Similarity	NPD4668	Phase 2
0.6209	Remote Similarity	NPD955	Approved
0.6207	Remote Similarity	NPD3141	Discontinued
0.6205	Remote Similarity	NPD3144	Approved
0.6205	Remote Similarity	NPD3145	Approved
0.6203	Remote Similarity	NPD5304	Approved
0.6203	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5303	Approved
0.6201	Remote Similarity	NPD2672	Discontinued
0.6201	Remote Similarity	NPD2366	Approved
0.6199	Remote Similarity	NPD9275	Approved
0.6199	Remote Similarity	NPD9278	Suspended
0.6199	Remote Similarity	NPD9276	Approved
0.6199	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD9274	Approved
0.6198	Remote Similarity	NPD6340	Approved
0.6198	Remote Similarity	NPD6339	Approved
0.6196	Remote Similarity	NPD1135	Approved
0.6196	Remote Similarity	NPD1133	Approved
0.6196	Remote Similarity	NPD1131	Approved
0.6196	Remote Similarity	NPD1129	Approved
0.6196	Remote Similarity	NPD1134	Approved
0.6194	Remote Similarity	NPD2234	Approved
0.6194	Remote Similarity	NPD2229	Approved
0.6194	Remote Similarity	NPD2228	Approved
0.619	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3823	Discontinued
0.619	Remote Similarity	NPD2791	Discontinued
0.6186	Remote Similarity	NPD5928	Phase 1
0.6185	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6658	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