NPASS Compound

Structure

NPC248462 OpenBabel07101718242D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.3371 3.3680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0606 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 1.2983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 2.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1250 2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 3.1254 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 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2024 2.9098 0.0000 N 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 0.5387 4.1254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 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 13 2 0 0 0 0 6 15 2 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 16 20 2 3 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.15
Volume:	324.073
LogP:	2.888
LogD:	2.214
LogS:	-3.463
# Rotatable Bonds:	1
TPSA:	51.1
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.866
Synthetic Accessibility Score:	3.819
Fsp3:	0.368
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:	-4.644
MDCK Permeability:	2.7537755158846267e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.436

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.489
Plasma Protein Binding (PPB):	69.57855987548828%
Volume Distribution (VD):	0.767
Pgp-substrate:	18.76336097717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.861
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.732
CYP2C19-substrate:	0.391
CYP2C9-inhibitor:	0.263
CYP2C9-substrate:	0.237
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.748

ADMET: Excretion

Clearance (CL):	3.774
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.085
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.489

Download Data

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

Natural Product: NPC248462

Natural Product ID:	NPC248462
*Common Name:**	Rhazinicine
IUPAC Name:	n.a.
Synonyms:	Rhazinicine
Standard InCHIKey:	TXWKUWXSHGUINF-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C19H20N2O2/c1-2-19-10-7-16(22)20-15-6-4-3-5-13(15)14-9-12-21(18(14)19)17(23)8-11-19/h3-6,9,12H,2,7-8,10-11H2,1H3,(H,20,22)/t19-/m0/s1
SMILES:	CC[C@]12CCC(=Nc3c(c4c2n(C(=O)CC1)cc4)cccc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL68701
PubChem CID:	639955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids

*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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4060.0	nM	PMID[450107]
NPT2	Others	Unspecified		Ratio	=	10.0	n.a.	PMID[450106]
NPT27	Others	Unspecified		IC50	=	3000.0	nM	PMID[450106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8120.0	nM	PMID[450107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6010.0	nM	PMID[450107]

☑ 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 NPC248462 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	295
0.1-0.2	2171
0.2-0.3	14020
0.3-0.4	17990
0.4-0.5	3403
0.5-0.6	2403
0.6-0.7	1849
0.7-0.8	533
0.8-0.85	27
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC64436
0.9119	High Similarity	NPC129721
0.8663	High Similarity	NPC159125
0.8427	Intermediate Similarity	NPC473763
0.8427	Intermediate Similarity	NPC117244
0.8229	Intermediate Similarity	NPC15840
0.8202	Intermediate Similarity	NPC478077
0.8192	Intermediate Similarity	NPC228835
0.8182	Intermediate Similarity	NPC113626
0.8156	Intermediate Similarity	NPC17059
0.8129	Intermediate Similarity	NPC56233
0.8101	Intermediate Similarity	NPC62749
0.8092	Intermediate Similarity	NPC158129
0.8081	Intermediate Similarity	NPC78020
0.8068	Intermediate Similarity	NPC11126
0.8068	Intermediate Similarity	NPC213468
0.8059	Intermediate Similarity	NPC194881
0.8057	Intermediate Similarity	NPC267885
0.8011	Intermediate Similarity	NPC234987
0.8011	Intermediate Similarity	NPC111275
0.8	Intermediate Similarity	NPC110500
0.8	Intermediate Similarity	NPC149155
0.8	Intermediate Similarity	NPC203468
0.8	Intermediate Similarity	NPC94752
0.7966	Intermediate Similarity	NPC248041
0.7966	Intermediate Similarity	NPC126709
0.7956	Intermediate Similarity	NPC472323
0.7955	Intermediate Similarity	NPC134586
0.7921	Intermediate Similarity	NPC91179
0.7912	Intermediate Similarity	NPC213629
0.791	Intermediate Similarity	NPC211997
0.791	Intermediate Similarity	NPC145885
0.791	Intermediate Similarity	NPC14113
0.791	Intermediate Similarity	NPC84827
0.7901	Intermediate Similarity	NPC235684
0.7898	Intermediate Similarity	NPC469938
0.7865	Intermediate Similarity	NPC55772
0.7865	Intermediate Similarity	NPC283219
0.7861	Intermediate Similarity	NPC149708
0.7833	Intermediate Similarity	NPC143533
0.7831	Intermediate Similarity	NPC300183
0.7816	Intermediate Similarity	NPC49954
0.7816	Intermediate Similarity	NPC474561
0.7816	Intermediate Similarity	NPC114637
0.7814	Intermediate Similarity	NPC321708
0.7811	Intermediate Similarity	NPC259644
0.7811	Intermediate Similarity	NPC469763
0.7811	Intermediate Similarity	NPC469760
0.7811	Intermediate Similarity	NPC73952
0.7811	Intermediate Similarity	NPC469765
0.7811	Intermediate Similarity	NPC25008
0.7811	Intermediate Similarity	NPC469786
0.7803	Intermediate Similarity	NPC478182
0.7796	Intermediate Similarity	NPC57994
0.7796	Intermediate Similarity	NPC289299
0.779	Intermediate Similarity	NPC165495
0.779	Intermediate Similarity	NPC472119
0.779	Intermediate Similarity	NPC258480
0.7789	Intermediate Similarity	NPC57398
0.7778	Intermediate Similarity	NPC65408
0.7778	Intermediate Similarity	NPC252338
0.7766	Intermediate Similarity	NPC131887
0.7766	Intermediate Similarity	NPC171317
0.7765	Intermediate Similarity	NPC211572
0.7765	Intermediate Similarity	NPC80597
0.7765	Intermediate Similarity	NPC70922
0.7765	Intermediate Similarity	NPC219336
0.7765	Intermediate Similarity	NPC212376
0.7765	Intermediate Similarity	NPC75540
0.7747	Intermediate Similarity	NPC472107
0.7747	Intermediate Similarity	NPC79062
0.7746	Intermediate Similarity	NPC282231
0.772	Intermediate Similarity	NPC54420
0.7717	Intermediate Similarity	NPC175474
0.7714	Intermediate Similarity	NPC160105
0.7713	Intermediate Similarity	NPC227582
0.7709	Intermediate Similarity	NPC15573
0.7709	Intermediate Similarity	NPC183662
0.7709	Intermediate Similarity	NPC217372
0.7708	Intermediate Similarity	NPC473376
0.7705	Intermediate Similarity	NPC66210
0.7701	Intermediate Similarity	NPC194640
0.7697	Intermediate Similarity	NPC469529
0.7688	Intermediate Similarity	NPC255229
0.7688	Intermediate Similarity	NPC279918
0.7688	Intermediate Similarity	NPC81229
0.7683	Intermediate Similarity	NPC104483
0.768	Intermediate Similarity	NPC233936
0.7674	Intermediate Similarity	NPC469762
0.767	Intermediate Similarity	NPC63751
0.7663	Intermediate Similarity	NPC204565
0.7641	Intermediate Similarity	NPC162860
0.7641	Intermediate Similarity	NPC478158
0.764	Intermediate Similarity	NPC477976
0.764	Intermediate Similarity	NPC161861
0.763	Intermediate Similarity	NPC293487
0.7622	Intermediate Similarity	NPC65215
0.7622	Intermediate Similarity	NPC173028
0.7616	Intermediate Similarity	NPC469785
0.7616	Intermediate Similarity	NPC285469
0.7609	Intermediate Similarity	NPC315555
0.7606	Intermediate Similarity	NPC294693
0.7606	Intermediate Similarity	NPC157828
0.7606	Intermediate Similarity	NPC195239
0.7604	Intermediate Similarity	NPC476073
0.76	Intermediate Similarity	NPC311276
0.7582	Intermediate Similarity	NPC71037
0.7579	Intermediate Similarity	NPC52557
0.7577	Intermediate Similarity	NPC238457
0.7571	Intermediate Similarity	NPC201700
0.7569	Intermediate Similarity	NPC133261
0.7568	Intermediate Similarity	NPC317030
0.7566	Intermediate Similarity	NPC11445
0.7561	Intermediate Similarity	NPC150259
0.756	Intermediate Similarity	NPC314372
0.7554	Intermediate Similarity	NPC62510
0.7542	Intermediate Similarity	NPC314603
0.7539	Intermediate Similarity	NPC293917
0.7529	Intermediate Similarity	NPC230869
0.7527	Intermediate Similarity	NPC24864
0.7527	Intermediate Similarity	NPC469896
0.7526	Intermediate Similarity	NPC262898
0.7514	Intermediate Similarity	NPC478183
0.7514	Intermediate Similarity	NPC326575
0.7514	Intermediate Similarity	NPC474707
0.7514	Intermediate Similarity	NPC54988
0.7514	Intermediate Similarity	NPC248454
0.7513	Intermediate Similarity	NPC260900
0.7512	Intermediate Similarity	NPC477714
0.7512	Intermediate Similarity	NPC281049
0.75	Intermediate Similarity	NPC478184
0.75	Intermediate Similarity	NPC477003
0.75	Intermediate Similarity	NPC471386
0.7487	Intermediate Similarity	NPC473640
0.7487	Intermediate Similarity	NPC474916
0.7474	Intermediate Similarity	NPC179701
0.7463	Intermediate Similarity	NPC477715
0.7461	Intermediate Similarity	NPC475506
0.746	Intermediate Similarity	NPC474177
0.7459	Intermediate Similarity	NPC99939
0.7459	Intermediate Similarity	NPC472122
0.7459	Intermediate Similarity	NPC24594
0.7459	Intermediate Similarity	NPC308931
0.7457	Intermediate Similarity	NPC207726
0.7456	Intermediate Similarity	NPC470440
0.7455	Intermediate Similarity	NPC314102
0.7455	Intermediate Similarity	NPC251722
0.745	Intermediate Similarity	NPC478157
0.7448	Intermediate Similarity	NPC100321
0.7443	Intermediate Similarity	NPC478185
0.7443	Intermediate Similarity	NPC16667
0.744	Intermediate Similarity	NPC190296
0.7437	Intermediate Similarity	NPC6865
0.7437	Intermediate Similarity	NPC153980
0.7435	Intermediate Similarity	NPC272483
0.7433	Intermediate Similarity	NPC111602
0.7433	Intermediate Similarity	NPC102338
0.7433	Intermediate Similarity	NPC196251
0.7433	Intermediate Similarity	NPC63199
0.743	Intermediate Similarity	NPC91895
0.743	Intermediate Similarity	NPC32534
0.7423	Intermediate Similarity	NPC155143
0.7421	Intermediate Similarity	NPC133366
0.7418	Intermediate Similarity	NPC59269
0.7404	Intermediate Similarity	NPC477175
0.7404	Intermediate Similarity	NPC477176
0.7404	Intermediate Similarity	NPC470729
0.7404	Intermediate Similarity	NPC470730
0.7403	Intermediate Similarity	NPC139763
0.7401	Intermediate Similarity	NPC40779
0.7401	Intermediate Similarity	NPC271797
0.7401	Intermediate Similarity	NPC21174
0.74	Intermediate Similarity	NPC54744
0.7399	Intermediate Similarity	NPC200214
0.7396	Intermediate Similarity	NPC470499
0.7394	Intermediate Similarity	NPC329858
0.7394	Intermediate Similarity	NPC472112
0.7394	Intermediate Similarity	NPC314333
0.7394	Intermediate Similarity	NPC83111
0.7394	Intermediate Similarity	NPC95783
0.7394	Intermediate Similarity	NPC154339
0.7387	Intermediate Similarity	NPC72956
0.7384	Intermediate Similarity	NPC105818
0.7384	Intermediate Similarity	NPC24678
0.7384	Intermediate Similarity	NPC40070
0.7382	Intermediate Similarity	NPC245916
0.7382	Intermediate Similarity	NPC472116
0.7368	Intermediate Similarity	NPC477177
0.7368	Intermediate Similarity	NPC475859
0.7368	Intermediate Similarity	NPC475969
0.7368	Intermediate Similarity	NPC470111
0.7368	Intermediate Similarity	NPC474877
0.7368	Intermediate Similarity	NPC267343
0.7363	Intermediate Similarity	NPC121903
0.7358	Intermediate Similarity	NPC74413
0.7354	Intermediate Similarity	NPC476460
0.7354	Intermediate Similarity	NPC472097
0.7351	Intermediate Similarity	NPC163055
0.735	Intermediate Similarity	NPC75634
0.7345	Intermediate Similarity	NPC242116

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 NPC248462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	540
0.2-0.3	861
0.3-0.4	1593
0.4-0.5	2478
0.5-0.6	2284
0.6-0.7	1028
0.7-0.8	178
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8363	Intermediate Similarity	NPD750	Phase 2
0.8306	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD6999	Discontinued
0.8187	Intermediate Similarity	NPD7944	Discontinued
0.8118	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD2511	Approved
0.8057	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD482	Approved
0.7989	Intermediate Similarity	NPD7619	Phase 3
0.7989	Intermediate Similarity	NPD5426	Phase 3
0.7989	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7618	Phase 3
0.7979	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD7666	Phase 3
0.7958	Intermediate Similarity	NPD7665	Phase 2
0.7955	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2094	Phase 2
0.7933	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2095	Phase 2
0.7933	Intermediate Similarity	NPD2092	Phase 2
0.7927	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4702	Approved
0.7892	Intermediate Similarity	NPD4703	Approved
0.7889	Intermediate Similarity	NPD2091	Phase 2
0.7889	Intermediate Similarity	NPD2096	Phase 2
0.7853	Intermediate Similarity	NPD7001	Phase 3
0.784	Intermediate Similarity	NPD2896	Discontinued
0.7819	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6987	Phase 1
0.7796	Intermediate Similarity	NPD4602	Approved
0.7784	Intermediate Similarity	NPD5505	Discontinued
0.7778	Intermediate Similarity	NPD201	Phase 2
0.7778	Intermediate Similarity	NPD200	Phase 2
0.776	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2336	Approved
0.7714	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6664	Approved
0.7688	Intermediate Similarity	NPD6665	Discontinued
0.7627	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4852	Phase 2
0.7614	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4397	Phase 1
0.7566	Intermediate Similarity	NPD2307	Discontinued
0.7563	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5555	Phase 1
0.7552	Intermediate Similarity	NPD5017	Discontinued
0.7539	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5901	Discontinued
0.7516	Intermediate Similarity	NPD3475	Approved
0.7516	Intermediate Similarity	NPD3476	Approved
0.7514	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5065	Approved
0.75	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7470	Discontinued
0.7472	Intermediate Similarity	NPD4638	Approved
0.7472	Intermediate Similarity	NPD4640	Approved
0.7472	Intermediate Similarity	NPD4639	Approved
0.7471	Intermediate Similarity	NPD4547	Phase 3
0.7459	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5100	Phase 3
0.7443	Intermediate Similarity	NPD5400	Approved
0.7442	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3717	Discontinued
0.7438	Intermediate Similarity	NPD2119	Approved
0.7438	Intermediate Similarity	NPD2118	Approved
0.7436	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6595	Phase 3
0.7405	Intermediate Similarity	NPD6178	Phase 3
0.7405	Intermediate Similarity	NPD7564	Discontinued
0.7399	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4499	Approved
0.7378	Intermediate Similarity	NPD3385	Approved
0.7374	Intermediate Similarity	NPD2844	Phase 3
0.7371	Intermediate Similarity	NPD4326	Phase 2
0.7368	Intermediate Similarity	NPD1661	Suspended
0.7366	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4075	Phase 2
0.736	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2809	Approved
0.7354	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8272	Phase 2
0.7347	Intermediate Similarity	NPD3947	Discontinued
0.734	Intermediate Similarity	NPD7234	Approved
0.734	Intermediate Similarity	NPD7233	Approved
0.7337	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4427	Phase 2
0.733	Intermediate Similarity	NPD5255	Approved
0.7326	Intermediate Similarity	NPD5809	Phase 3
0.732	Intermediate Similarity	NPD4600	Approved
0.732	Intermediate Similarity	NPD4601	Approved
0.7317	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7168	Phase 3
0.7303	Intermediate Similarity	NPD3583	Phase 2
0.7287	Intermediate Similarity	NPD4988	Discontinued
0.7286	Intermediate Similarity	NPD4520	Approved
0.7278	Intermediate Similarity	NPD5862	Discovery
0.7278	Intermediate Similarity	NPD1722	Approved
0.7273	Intermediate Similarity	NPD4028	Approved
0.7273	Intermediate Similarity	NPD4030	Approved
0.7273	Intermediate Similarity	NPD4029	Approved
0.7264	Intermediate Similarity	NPD8093	Discontinued
0.7263	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7187	Phase 2
0.7243	Intermediate Similarity	NPD5897	Approved
0.7243	Intermediate Similarity	NPD5898	Approved
0.7243	Intermediate Similarity	NPD5899	Approved
0.7239	Intermediate Similarity	NPD3654	Approved
0.7236	Intermediate Similarity	NPD2916	Discontinued
0.7235	Intermediate Similarity	NPD2006	Phase 2
0.7234	Intermediate Similarity	NPD7026	Phase 2
0.7228	Intermediate Similarity	NPD8094	Discontinued
0.7228	Intermediate Similarity	NPD2144	Approved
0.7228	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6165	Phase 2
0.7225	Intermediate Similarity	NPD2430	Phase 2
0.7225	Intermediate Similarity	NPD6164	Phase 2
0.7222	Intermediate Similarity	NPD5611	Phase 2
0.7222	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6281	Approved
0.7209	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1631	Approved
0.7206	Intermediate Similarity	NPD6710	Phase 3
0.7206	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4848	Phase 1
0.7196	Intermediate Similarity	NPD4948	Discontinued
0.7196	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8431	Approved
0.7193	Intermediate Similarity	NPD3813	Approved
0.7192	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7970	Approved
0.7189	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4805	Approved
0.7176	Intermediate Similarity	NPD5020	Approved
0.7174	Intermediate Similarity	NPD5471	Phase 3
0.7173	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3944	Approved
0.7169	Intermediate Similarity	NPD3942	Approved
0.7167	Intermediate Similarity	NPD2720	Phase 1
0.7167	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD786	Approved
0.7158	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4334	Discontinued
0.7156	Intermediate Similarity	NPD7824	Approved
0.7151	Intermediate Similarity	NPD6452	Discontinued
0.7151	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2882	Phase 1
0.7143	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD484	Approved
0.7143	Intermediate Similarity	NPD2305	Discontinued
0.7136	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3430	Approved
0.7135	Intermediate Similarity	NPD8123	Approved
0.7135	Intermediate Similarity	NPD2753	Discontinued
0.7135	Intermediate Similarity	NPD8122	Approved
0.7135	Intermediate Similarity	NPD3431	Approved
0.7128	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5636	Discontinued
0.7126	Intermediate Similarity	NPD3100	Discontinued
0.712	Intermediate Similarity	NPD3321	Discontinued
0.7113	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD3038	Discontinued
0.7111	Intermediate Similarity	NPD5088	Discontinued
0.711	Intermediate Similarity	NPD7469	Discontinued
0.7105	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD2837	Discontinued
0.7097	Intermediate Similarity	NPD4076	Approved
0.7097	Intermediate Similarity	NPD4079	Approved
0.7095	Intermediate Similarity	NPD7603	Discontinued
0.7088	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2172	Phase 1
0.7083	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6044	Discontinued
0.7081	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3238	Discontinued
0.7079	Intermediate Similarity	NPD2581	Approved
0.7079	Intermediate Similarity	NPD2582	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