NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.08
Volume:	240.28
LogP:	0.625
LogD:	0.799
LogS:	-3.091
# Rotatable Bonds:	1
TPSA:	89.11
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	3.218
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.182
MDCK Permeability:	4.166935468674637e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.397
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	65.37726593017578%
Volume Distribution (VD):	1.095
Pgp-substrate:	24.14815330505371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.865
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.484
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.602
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	4.634
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.534
AMES Toxicity:	0.776
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.563
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.485
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC306376

Natural Product ID:	NPC306376
*Common Name:**	Brunnein A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KSNGZQWONODVBX-NSHDSACASA-N
Standard InCHI:	InChI=1S/C13H12N2O3/c1-6-12-9(5-11(14-6)13(17)18)8-3-2-7(16)4-10(8)15-12/h2-4,11,15-16H,5H2,1H3,(H,17,18)/t11-/m0/s1
SMILES:	OC(=O)[C@H]1N=C(C)c2c(C1)c1ccc(cc1[nH]2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399231
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO27298	Cortinarius brunneus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17854153]
NPO27298	Cortinarius brunneus	Species	Cortinariaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Inhibition	<	50.0	%	PMID[522911]
NPT914	Individual Protein	Acetylcholinesterase	Bos taurus	Inhibition	<	50.0	%	PMID[522911]

☑ 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 NPC306376 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	324
0.1-0.2	2485
0.2-0.3	13365
0.3-0.4	7715
0.4-0.5	12690
0.5-0.6	3380
0.6-0.7	2006
0.7-0.8	665
0.8-0.85	60
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9086	High Similarity	NPC72980
0.8962	High Similarity	NPC276517
0.8883	High Similarity	NPC476098
0.8698	High Similarity	NPC39679
0.8673	High Similarity	NPC330009
0.8624	High Similarity	NPC315491
0.8624	High Similarity	NPC45459
0.8586	High Similarity	NPC303658
0.849	Intermediate Similarity	NPC134848
0.8469	Intermediate Similarity	NPC87413
0.8432	Intermediate Similarity	NPC46580
0.8429	Intermediate Similarity	NPC213308
0.8415	Intermediate Similarity	NPC212535
0.8392	Intermediate Similarity	NPC74969
0.8392	Intermediate Similarity	NPC3207
0.837	Intermediate Similarity	NPC84478
0.8333	Intermediate Similarity	NPC474409
0.8324	Intermediate Similarity	NPC94943
0.8316	Intermediate Similarity	NPC210828
0.8316	Intermediate Similarity	NPC86834
0.8283	Intermediate Similarity	NPC23294
0.8276	Intermediate Similarity	NPC60621
0.8274	Intermediate Similarity	NPC325297
0.827	Intermediate Similarity	NPC190007
0.8265	Intermediate Similarity	NPC4687
0.8251	Intermediate Similarity	NPC219336
0.8232	Intermediate Similarity	NPC303951
0.8218	Intermediate Similarity	NPC264285
0.8213	Intermediate Similarity	NPC194740
0.8209	Intermediate Similarity	NPC469928
0.8197	Intermediate Similarity	NPC183662
0.8197	Intermediate Similarity	NPC217372
0.8197	Intermediate Similarity	NPC15573
0.8173	Intermediate Similarity	NPC270918
0.8137	Intermediate Similarity	NPC174760
0.8128	Intermediate Similarity	NPC473041
0.8116	Intermediate Similarity	NPC319232
0.8116	Intermediate Similarity	NPC24370
0.8116	Intermediate Similarity	NPC214142
0.8098	Intermediate Similarity	NPC96890
0.8083	Intermediate Similarity	NPC156704
0.8081	Intermediate Similarity	NPC183777
0.8081	Intermediate Similarity	NPC88008
0.8079	Intermediate Similarity	NPC305984
0.8077	Intermediate Similarity	NPC261251
0.8077	Intermediate Similarity	NPC304307
0.8077	Intermediate Similarity	NPC124920
0.8077	Intermediate Similarity	NPC118559
0.8077	Intermediate Similarity	NPC34580
0.8068	Intermediate Similarity	NPC21638
0.8043	Intermediate Similarity	NPC267885
0.8039	Intermediate Similarity	NPC247803
0.8038	Intermediate Similarity	NPC100547
0.8031	Intermediate Similarity	NPC242209
0.803	Intermediate Similarity	NPC148183
0.803	Intermediate Similarity	NPC152768
0.8023	Intermediate Similarity	NPC141353
0.801	Intermediate Similarity	NPC473317
0.8	Intermediate Similarity	NPC223409
0.8	Intermediate Similarity	NPC322135
0.8	Intermediate Similarity	NPC95240
0.799	Intermediate Similarity	NPC70956
0.799	Intermediate Similarity	NPC153042
0.799	Intermediate Similarity	NPC141454
0.799	Intermediate Similarity	NPC249583
0.799	Intermediate Similarity	NPC243834
0.799	Intermediate Similarity	NPC321428
0.7989	Intermediate Similarity	NPC110500
0.7989	Intermediate Similarity	NPC149155
0.7989	Intermediate Similarity	NPC203468
0.798	Intermediate Similarity	NPC116238
0.798	Intermediate Similarity	NPC118228
0.7971	Intermediate Similarity	NPC16352
0.797	Intermediate Similarity	NPC12344
0.7962	Intermediate Similarity	NPC14288
0.7961	Intermediate Similarity	NPC150239
0.7957	Intermediate Similarity	NPC248041
0.7957	Intermediate Similarity	NPC126709
0.7957	Intermediate Similarity	NPC88363
0.7937	Intermediate Similarity	NPC314002
0.7929	Intermediate Similarity	NPC165599
0.7925	Intermediate Similarity	NPC54803
0.7925	Intermediate Similarity	NPC321592
0.7914	Intermediate Similarity	NPC469896
0.7906	Intermediate Similarity	NPC221873
0.7902	Intermediate Similarity	NPC169402
0.7895	Intermediate Similarity	NPC125597
0.7895	Intermediate Similarity	NPC179287
0.7887	Intermediate Similarity	NPC323752
0.7887	Intermediate Similarity	NPC473105
0.7887	Intermediate Similarity	NPC284888
0.7887	Intermediate Similarity	NPC323198
0.7885	Intermediate Similarity	NPC220851
0.7884	Intermediate Similarity	NPC204717
0.7879	Intermediate Similarity	NPC475085
0.7879	Intermediate Similarity	NPC475112
0.7879	Intermediate Similarity	NPC291535
0.7876	Intermediate Similarity	NPC99666
0.7861	Intermediate Similarity	NPC283219
0.785	Intermediate Similarity	NPC245055
0.785	Intermediate Similarity	NPC33064
0.7847	Intermediate Similarity	NPC51388
0.7831	Intermediate Similarity	NPC176127
0.7831	Intermediate Similarity	NPC220765
0.7824	Intermediate Similarity	NPC470784
0.7821	Intermediate Similarity	NPC285469
0.7811	Intermediate Similarity	NPC283117
0.7807	Intermediate Similarity	NPC111275
0.7801	Intermediate Similarity	NPC235684
0.7801	Intermediate Similarity	NPC171171
0.7795	Intermediate Similarity	NPC326634
0.7794	Intermediate Similarity	NPC308137
0.7794	Intermediate Similarity	NPC310211
0.7789	Intermediate Similarity	NPC199277
0.7789	Intermediate Similarity	NPC135887
0.7778	Intermediate Similarity	NPC184680
0.7778	Intermediate Similarity	NPC249040
0.7778	Intermediate Similarity	NPC184408
0.7772	Intermediate Similarity	NPC78020
0.7772	Intermediate Similarity	NPC475910
0.7761	Intermediate Similarity	NPC300156
0.7756	Intermediate Similarity	NPC471080
0.7756	Intermediate Similarity	NPC469592
0.7745	Intermediate Similarity	NPC294375
0.7745	Intermediate Similarity	NPC9894
0.7742	Intermediate Similarity	NPC470785
0.7742	Intermediate Similarity	NPC82472
0.7739	Intermediate Similarity	NPC471944
0.7729	Intermediate Similarity	NPC293151
0.7725	Intermediate Similarity	NPC91179
0.7723	Intermediate Similarity	NPC244741
0.7713	Intermediate Similarity	NPC14113
0.7713	Intermediate Similarity	NPC145885
0.7713	Intermediate Similarity	NPC84827
0.771	Intermediate Similarity	NPC260434
0.7708	Intermediate Similarity	NPC160381
0.7692	Intermediate Similarity	NPC96321
0.7692	Intermediate Similarity	NPC469734
0.7688	Intermediate Similarity	NPC329747
0.7688	Intermediate Similarity	NPC6982
0.7681	Intermediate Similarity	NPC322064
0.768	Intermediate Similarity	NPC314333
0.768	Intermediate Similarity	NPC83111
0.7672	Intermediate Similarity	NPC55772
0.7664	Intermediate Similarity	NPC326363
0.7662	Intermediate Similarity	NPC53144
0.7656	Intermediate Similarity	NPC208084
0.7656	Intermediate Similarity	NPC74360
0.7653	Intermediate Similarity	NPC106937
0.765	Intermediate Similarity	NPC16667
0.7647	Intermediate Similarity	NPC34508
0.7635	Intermediate Similarity	NPC53344
0.7635	Intermediate Similarity	NPC193777
0.7629	Intermediate Similarity	NPC246700
0.7629	Intermediate Similarity	NPC175474
0.7629	Intermediate Similarity	NPC321708
0.7629	Intermediate Similarity	NPC128751
0.7628	Intermediate Similarity	NPC474701
0.7624	Intermediate Similarity	NPC285558
0.7621	Intermediate Similarity	NPC264176
0.7621	Intermediate Similarity	NPC294620
0.7619	Intermediate Similarity	NPC184964
0.7617	Intermediate Similarity	NPC315555
0.7615	Intermediate Similarity	NPC15801
0.7614	Intermediate Similarity	NPC131017
0.7613	Intermediate Similarity	NPC178858
0.7608	Intermediate Similarity	NPC469594
0.7608	Intermediate Similarity	NPC46561
0.7606	Intermediate Similarity	NPC303225
0.7596	Intermediate Similarity	NPC183407
0.7594	Intermediate Similarity	NPC122436
0.7593	Intermediate Similarity	NPC132329
0.759	Intermediate Similarity	NPC469497
0.759	Intermediate Similarity	NPC106833
0.7588	Intermediate Similarity	NPC72211
0.7586	Intermediate Similarity	NPC476106
0.7585	Intermediate Similarity	NPC39500
0.7585	Intermediate Similarity	NPC89508
0.7583	Intermediate Similarity	NPC198503
0.7579	Intermediate Similarity	NPC472443
0.7576	Intermediate Similarity	NPC70259
0.7573	Intermediate Similarity	NPC82370
0.7569	Intermediate Similarity	NPC207726
0.7562	Intermediate Similarity	NPC232727
0.7554	Intermediate Similarity	NPC282231
0.7542	Intermediate Similarity	NPC37548
0.7538	Intermediate Similarity	NPC63199
0.7538	Intermediate Similarity	NPC196251
0.7538	Intermediate Similarity	NPC102338
0.7538	Intermediate Similarity	NPC77555
0.7538	Intermediate Similarity	NPC74153
0.7538	Intermediate Similarity	NPC111602
0.7536	Intermediate Similarity	NPC48353
0.7536	Intermediate Similarity	NPC316981
0.7536	Intermediate Similarity	NPC219087
0.7536	Intermediate Similarity	NPC276657
0.7535	Intermediate Similarity	NPC471762
0.7535	Intermediate Similarity	NPC274640
0.7534	Intermediate Similarity	NPC6786
0.7526	Intermediate Similarity	NPC62749

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 NPC306376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	586
0.2-0.3	885
0.3-0.4	1098
0.4-0.5	2711
0.5-0.6	2640
0.6-0.7	911
0.7-0.8	117
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8624	High Similarity	NPD484	Approved
0.8131	Intermediate Similarity	NPD2916	Discontinued
0.8066	Intermediate Similarity	NPD2844	Phase 3
0.7989	Intermediate Similarity	NPD482	Approved
0.7951	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7948	Phase 1
0.78	Intermediate Similarity	NPD5901	Discontinued
0.7744	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD750	Phase 2
0.7737	Intermediate Similarity	NPD2094	Phase 2
0.7737	Intermediate Similarity	NPD2092	Phase 2
0.7737	Intermediate Similarity	NPD2095	Phase 2
0.773	Intermediate Similarity	NPD1325	Approved
0.773	Intermediate Similarity	NPD1326	Approved
0.7696	Intermediate Similarity	NPD2096	Phase 2
0.7696	Intermediate Similarity	NPD2091	Phase 2
0.768	Intermediate Similarity	NPD4499	Approved
0.7656	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD802	Phase 2
0.7638	Intermediate Similarity	NPD3814	Phase 1
0.7626	Intermediate Similarity	NPD5003	Discontinued
0.7608	Intermediate Similarity	NPD5632	Approved
0.7606	Intermediate Similarity	NPD7603	Discontinued
0.7586	Intermediate Similarity	NPD3003	Approved
0.7586	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4511	Phase 1
0.7552	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1768	Approved
0.7512	Intermediate Similarity	NPD4601	Approved
0.7512	Intermediate Similarity	NPD4600	Approved
0.75	Intermediate Similarity	NPD2565	Phase 2
0.75	Intermediate Similarity	NPD3243	Approved
0.75	Intermediate Similarity	NPD2564	Approved
0.7488	Intermediate Similarity	NPD7470	Discontinued
0.7466	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD1534	Approved
0.7427	Intermediate Similarity	NPD5658	Approved
0.7426	Intermediate Similarity	NPD4501	Approved
0.7426	Intermediate Similarity	NPD4500	Approved
0.7398	Intermediate Similarity	NPD4948	Discontinued
0.7398	Intermediate Similarity	NPD2383	Phase 1
0.7387	Intermediate Similarity	NPD1038	Approved
0.7387	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2176	Approved
0.7376	Intermediate Similarity	NPD2175	Phase 3
0.7376	Intermediate Similarity	NPD2177	Approved
0.7366	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD4885	Approved
0.7343	Intermediate Similarity	NPD6376	Discontinued
0.7327	Intermediate Similarity	NPD3259	Approved
0.7313	Intermediate Similarity	NPD5512	Phase 3
0.731	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1392	Approved
0.7282	Intermediate Similarity	NPD8098	Approved
0.7264	Intermediate Similarity	NPD4418	Discontinued
0.7264	Intermediate Similarity	NPD5612	Discontinued
0.7254	Intermediate Similarity	NPD6159	Phase 2
0.7248	Intermediate Similarity	NPD4845	Discontinued
0.7246	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4373	Phase 2
0.7217	Intermediate Similarity	NPD5903	Approved
0.7217	Intermediate Similarity	NPD5902	Approved
0.7209	Intermediate Similarity	NPD6242	Discontinued
0.7207	Intermediate Similarity	NPD1592	Phase 3
0.7206	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8395	Approved
0.7206	Intermediate Similarity	NPD8396	Approved
0.7205	Intermediate Similarity	NPD5482	Discontinued
0.7204	Intermediate Similarity	NPD8096	Phase 3
0.7204	Intermediate Similarity	NPD8097	Phase 3
0.7204	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD8363	Approved
0.7185	Intermediate Similarity	NPD8364	Approved
0.7182	Intermediate Similarity	NPD4952	Phase 3
0.7179	Intermediate Similarity	NPD5445	Approved
0.7179	Intermediate Similarity	NPD6452	Discontinued
0.7157	Intermediate Similarity	NPD7946	Pre-registration
0.715	Intermediate Similarity	NPD5065	Approved
0.715	Intermediate Similarity	NPD2920	Discontinued
0.7143	Intermediate Similarity	NPD5140	Approved
0.7143	Intermediate Similarity	NPD3178	Discontinued
0.7143	Intermediate Similarity	NPD5138	Approved
0.7136	Intermediate Similarity	NPD4897	Phase 2
0.7125	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4602	Approved
0.709	Intermediate Similarity	NPD1685	Approved
0.709	Intermediate Similarity	NPD1684	Approved
0.7083	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6665	Discontinued
0.7079	Intermediate Similarity	NPD5937	Approved
0.7078	Intermediate Similarity	NPD8427	Approved
0.7078	Intermediate Similarity	NPD8429	Approved
0.7078	Intermediate Similarity	NPD8428	Approved
0.7078	Intermediate Similarity	NPD8467	Approved
0.7078	Intermediate Similarity	NPD8466	Approved
0.7078	Intermediate Similarity	NPD8465	Approved
0.7075	Intermediate Similarity	NPD5936	Approved
0.7075	Intermediate Similarity	NPD5939	Approved
0.7073	Intermediate Similarity	NPD7778	Approved
0.7073	Intermediate Similarity	NPD7777	Approved
0.7073	Intermediate Similarity	NPD53	Approved
0.7068	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7956	Approved
0.7064	Intermediate Similarity	NPD7955	Approved
0.7048	Intermediate Similarity	NPD7452	Approved
0.7048	Intermediate Similarity	NPD7222	Phase 2
0.7048	Intermediate Similarity	NPD7453	Approved
0.7048	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2794	Discontinued
0.7039	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6985	Discontinued
0.7037	Intermediate Similarity	NPD3354	Phase 2
0.703	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4463	Approved
0.7027	Intermediate Similarity	NPD4462	Approved
0.7019	Intermediate Similarity	NPD8073	Approved
0.7014	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2510	Approved
0.7014	Intermediate Similarity	NPD2509	Approved
0.701	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7558	Phase 2
0.7009	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7194	Discontinued
0.7005	Intermediate Similarity	NPD3258	Approved
0.7005	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6962	Phase 2
0.6995	Remote Similarity	NPD5416	Discontinued
0.6995	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7865	Approved
0.6989	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6158	Phase 2
0.6986	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4506	Discontinued
0.6977	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5429	Discontinued
0.6964	Remote Similarity	NPD8425	Approved
0.6964	Remote Similarity	NPD8426	Approved
0.6964	Remote Similarity	NPD8460	Approved
0.6964	Remote Similarity	NPD8459	Approved
0.6963	Remote Similarity	NPD1631	Approved
0.6963	Remote Similarity	NPD8093	Discontinued
0.6954	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5426	Phase 3
0.6952	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7853	Phase 2
0.6944	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5506	Approved
0.6941	Remote Similarity	NPD5507	Approved
0.6937	Remote Similarity	NPD7994	Phase 2
0.6937	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5596	Phase 2
0.6934	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5897	Approved
0.6919	Remote Similarity	NPD6595	Phase 3
0.6919	Remote Similarity	NPD5898	Approved
0.6919	Remote Similarity	NPD7957	Phase 1
0.6919	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5899	Approved
0.6919	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7803	Approved
0.6916	Remote Similarity	NPD4502	Phase 2
0.6915	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4397	Phase 1
0.6908	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6176	Phase 1
0.6905	Remote Similarity	NPD8072	Approved
0.6898	Remote Similarity	NPD3257	Approved
0.6898	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8358	Approved
0.6889	Remote Similarity	NPD3746	Discontinued
0.6888	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6290	Phase 2
0.6884	Remote Similarity	NPD4204	Approved
0.6884	Remote Similarity	NPD5866	Approved
0.6884	Remote Similarity	NPD4203	Approved
0.6884	Remote Similarity	NPD3330	Phase 1
0.6884	Remote Similarity	NPD7069	Discontinued
0.6881	Remote Similarity	NPD7395	Discontinued
0.6878	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6716	Phase 1
0.687	Remote Similarity	NPD6517	Phase 3
0.6869	Remote Similarity	NPD8386	Phase 2

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