NPASS Compound

Structure

CID314102 OpenBabel06191716122D 21 23 0 0 0 0 0 0 0 0999 V2000 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 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 18 2 0 0 0 0 6 19 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 20 2 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.15
Volume:	309.776
LogP:	4.383
LogD:	3.983
LogS:	-4.663
# Rotatable Bonds:	3
TPSA:	16.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	2.007
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.682
MDCK Permeability:	1.6894562577363104e-05
Pgp-inhibitor:	0.335
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	96.8379135131836%
Volume Distribution (VD):	1.281
Pgp-substrate:	2.236081123352051%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.838
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.737
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	5.335
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.623
Human Hepatotoxicity (H-HT):	0.265
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.921
Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.837
Carcinogencity:	0.807
Eye Corrosion:	0.024
Eye Irritation:	0.99
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC314102

Natural Product ID:	NPC314102
*Common Name:**	N,N-Dimethyl-4-[(E)-2-Quinolin-4-Ylethenyl]Aniline
IUPAC Name:	N,N-dimethyl-4-[(E)-2-quinolin-4-ylethenyl]aniline
Synonyms:
Standard InCHIKey:	CIXDQQGMRYRUQA-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C19H18N2/c1-21(2)17-11-8-15(9-12-17)7-10-16-13-14-20-19-6-4-3-5-18(16)19/h3-14H,1-2H3/b10-7+
SMILES:	CN(c1ccc(cc1)/C=C/c1ccnc2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1884481
PubChem CID:	668053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives

*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

☑ 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
Potency	8

Activity Type	# Activity
Cell Line	1
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[480333]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[480333]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[480333]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[480333]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[480333]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[480333]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[480333]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[480333]

☑ 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 NPC314102 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	1035
0.1-0.2	12272
0.2-0.3	17703
0.3-0.4	5964
0.4-0.5	2294
0.5-0.6	1947
0.6-0.7	1026
0.7-0.8	338
0.8-0.85	96
0.85-0.9	17
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251722
0.9185	High Similarity	NPC169433
0.8992	High Similarity	NPC46358
0.8832	High Similarity	NPC150259
0.8811	High Similarity	NPC40070
0.8779	High Similarity	NPC122718
0.8605	High Similarity	NPC162689
0.8605	High Similarity	NPC54102
0.8605	High Similarity	NPC91958
0.8581	High Similarity	NPC56765
0.8571	High Similarity	NPC73767
0.8542	High Similarity	NPC470111
0.8529	High Similarity	NPC282398
0.8527	High Similarity	NPC81561
0.8523	High Similarity	NPC215584
0.8523	High Similarity	NPC44773
0.8511	High Similarity	NPC469768
0.8511	High Similarity	NPC469779
0.8511	High Similarity	NPC469783
0.8511	High Similarity	NPC469780
0.8511	High Similarity	NPC469784
0.8511	High Similarity	NPC469761
0.8511	High Similarity	NPC469767
0.8493	Intermediate Similarity	NPC470233
0.8473	Intermediate Similarity	NPC215519
0.8451	Intermediate Similarity	NPC469766
0.845	Intermediate Similarity	NPC148140
0.8446	Intermediate Similarity	NPC51054
0.844	Intermediate Similarity	NPC315348
0.844	Intermediate Similarity	NPC32002
0.844	Intermediate Similarity	NPC110126
0.844	Intermediate Similarity	NPC316811
0.8435	Intermediate Similarity	NPC325903
0.8429	Intermediate Similarity	NPC84911
0.8425	Intermediate Similarity	NPC53947
0.8414	Intermediate Similarity	NPC179787
0.8414	Intermediate Similarity	NPC201380
0.8392	Intermediate Similarity	NPC20144
0.8385	Intermediate Similarity	NPC297486
0.8385	Intermediate Similarity	NPC471402
0.8385	Intermediate Similarity	NPC240136
0.8357	Intermediate Similarity	NPC96102
0.8357	Intermediate Similarity	NPC261195
0.8357	Intermediate Similarity	NPC29886
0.8356	Intermediate Similarity	NPC321911
0.8345	Intermediate Similarity	NPC63545
0.8345	Intermediate Similarity	NPC288838
0.8333	Intermediate Similarity	NPC206819
0.8333	Intermediate Similarity	NPC318065
0.8321	Intermediate Similarity	NPC143603
0.831	Intermediate Similarity	NPC104483
0.8298	Intermediate Similarity	NPC105127
0.8289	Intermediate Similarity	NPC478182
0.8289	Intermediate Similarity	NPC90723
0.8288	Intermediate Similarity	NPC469811
0.8276	Intermediate Similarity	NPC86288
0.8261	Intermediate Similarity	NPC69914
0.8222	Intermediate Similarity	NPC476322
0.8188	Intermediate Similarity	NPC476131
0.8156	Intermediate Similarity	NPC198988
0.8151	Intermediate Similarity	NPC314372
0.8148	Intermediate Similarity	NPC290094
0.8146	Intermediate Similarity	NPC129721
0.8146	Intermediate Similarity	NPC216643
0.8146	Intermediate Similarity	NPC286427
0.8138	Intermediate Similarity	NPC190296
0.8134	Intermediate Similarity	NPC265605
0.8134	Intermediate Similarity	NPC48564
0.8134	Intermediate Similarity	NPC182570
0.8125	Intermediate Similarity	NPC279081
0.8125	Intermediate Similarity	NPC59084
0.8125	Intermediate Similarity	NPC2949
0.8092	Intermediate Similarity	NPC293487
0.8092	Intermediate Similarity	NPC477591
0.8092	Intermediate Similarity	NPC41257
0.8079	Intermediate Similarity	NPC476464
0.8074	Intermediate Similarity	NPC329825
0.8071	Intermediate Similarity	NPC256893
0.8071	Intermediate Similarity	NPC82295
0.8069	Intermediate Similarity	NPC473868
0.8069	Intermediate Similarity	NPC63157
0.8056	Intermediate Similarity	NPC88097
0.8054	Intermediate Similarity	NPC24678
0.8054	Intermediate Similarity	NPC33421
0.8054	Intermediate Similarity	NPC105818
0.8052	Intermediate Similarity	NPC317105
0.8041	Intermediate Similarity	NPC21605
0.8027	Intermediate Similarity	NPC285731
0.8026	Intermediate Similarity	NPC236711
0.8	Intermediate Similarity	NPC230002
0.7987	Intermediate Similarity	NPC280852
0.7987	Intermediate Similarity	NPC470203
0.7984	Intermediate Similarity	NPC27802
0.7974	Intermediate Similarity	NPC135141
0.7974	Intermediate Similarity	NPC92796
0.7973	Intermediate Similarity	NPC143872
0.7972	Intermediate Similarity	NPC325252
0.7971	Intermediate Similarity	NPC169625
0.7971	Intermediate Similarity	NPC202957
0.7962	Intermediate Similarity	NPC194411
0.7949	Intermediate Similarity	NPC478183
0.7947	Intermediate Similarity	NPC469765
0.7947	Intermediate Similarity	NPC200214
0.7947	Intermediate Similarity	NPC469763
0.7947	Intermediate Similarity	NPC469786
0.7947	Intermediate Similarity	NPC138842
0.7947	Intermediate Similarity	NPC25008
0.7947	Intermediate Similarity	NPC73952
0.7947	Intermediate Similarity	NPC469760
0.7947	Intermediate Similarity	NPC259644
0.7943	Intermediate Similarity	NPC179365
0.7943	Intermediate Similarity	NPC475450
0.7943	Intermediate Similarity	NPC101165
0.7935	Intermediate Similarity	NPC478184
0.7922	Intermediate Similarity	NPC470204
0.7922	Intermediate Similarity	NPC122141
0.7919	Intermediate Similarity	NPC471957
0.7911	Intermediate Similarity	NPC201634
0.7905	Intermediate Similarity	NPC159856
0.7899	Intermediate Similarity	NPC166424
0.7899	Intermediate Similarity	NPC245244
0.7899	Intermediate Similarity	NPC146373
0.7895	Intermediate Similarity	NPC70922
0.7895	Intermediate Similarity	NPC80597
0.7895	Intermediate Similarity	NPC476219
0.7895	Intermediate Similarity	NPC75540
0.7895	Intermediate Similarity	NPC212376
0.7895	Intermediate Similarity	NPC211572
0.7872	Intermediate Similarity	NPC22079
0.7871	Intermediate Similarity	NPC225018
0.7871	Intermediate Similarity	NPC478185
0.7857	Intermediate Similarity	NPC89490
0.7848	Intermediate Similarity	NPC91895
0.7842	Intermediate Similarity	NPC250361
0.7834	Intermediate Similarity	NPC56233
0.7812	Intermediate Similarity	NPC275305
0.7812	Intermediate Similarity	NPC37423
0.7801	Intermediate Similarity	NPC329896
0.7801	Intermediate Similarity	NPC475090
0.7801	Intermediate Similarity	NPC475105
0.7801	Intermediate Similarity	NPC473587
0.7799	Intermediate Similarity	NPC82331
0.7785	Intermediate Similarity	NPC469525
0.7785	Intermediate Similarity	NPC63751
0.7778	Intermediate Similarity	NPC476297
0.7778	Intermediate Similarity	NPC34844
0.7763	Intermediate Similarity	NPC470823
0.7762	Intermediate Similarity	NPC473930
0.7761	Intermediate Similarity	NPC476566
0.7755	Intermediate Similarity	NPC115611
0.7752	Intermediate Similarity	NPC76540
0.7752	Intermediate Similarity	NPC231655
0.7746	Intermediate Similarity	NPC475428
0.7742	Intermediate Similarity	NPC475990
0.7742	Intermediate Similarity	NPC221786
0.7742	Intermediate Similarity	NPC6436
0.7742	Intermediate Similarity	NPC474880
0.7736	Intermediate Similarity	NPC32534
0.773	Intermediate Similarity	NPC473762
0.7727	Intermediate Similarity	NPC469785
0.7716	Intermediate Similarity	NPC68354
0.7716	Intermediate Similarity	NPC157583
0.7714	Intermediate Similarity	NPC476140
0.7712	Intermediate Similarity	NPC141926
0.7702	Intermediate Similarity	NPC297034
0.7698	Intermediate Similarity	NPC27740
0.7692	Intermediate Similarity	NPC229173
0.7677	Intermediate Similarity	NPC469762
0.7669	Intermediate Similarity	NPC215795
0.7669	Intermediate Similarity	NPC176199
0.7667	Intermediate Similarity	NPC470440
0.766	Intermediate Similarity	NPC471311
0.766	Intermediate Similarity	NPC471313
0.7658	Intermediate Similarity	NPC2165
0.7658	Intermediate Similarity	NPC274229
0.7658	Intermediate Similarity	NPC195507
0.7654	Intermediate Similarity	NPC150048
0.7654	Intermediate Similarity	NPC203754
0.7654	Intermediate Similarity	NPC474958
0.7647	Intermediate Similarity	NPC216713
0.761	Intermediate Similarity	NPC474561
0.761	Intermediate Similarity	NPC49954
0.7603	Intermediate Similarity	NPC218268
0.7595	Intermediate Similarity	NPC311276
0.7593	Intermediate Similarity	NPC471579
0.758	Intermediate Similarity	NPC255229
0.758	Intermediate Similarity	NPC81229
0.7566	Intermediate Similarity	NPC477974
0.7564	Intermediate Similarity	NPC193740
0.7564	Intermediate Similarity	NPC167635
0.7562	Intermediate Similarity	NPC201700
0.7561	Intermediate Similarity	NPC12649
0.7554	Intermediate Similarity	NPC41174
0.755	Intermediate Similarity	NPC204141
0.7532	Intermediate Similarity	NPC282231
0.7531	Intermediate Similarity	NPC477611
0.7517	Intermediate Similarity	NPC284635
0.7516	Intermediate Similarity	NPC97343
0.7515	Intermediate Similarity	NPC314919
0.75	Intermediate Similarity	NPC237188

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 NPC314102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	855
0.2-0.3	942
0.3-0.4	1920
0.4-0.5	2157
0.5-0.6	1725
0.6-0.7	859
0.7-0.8	200
0.8-0.85	39
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9209	High Similarity	NPD4547	Phase 3
0.9154	High Similarity	NPD2118	Approved
0.9154	High Similarity	NPD2119	Approved
0.903	High Similarity	NPD3385	Approved
0.8889	High Similarity	NPD3944	Approved
0.8889	High Similarity	NPD3942	Approved
0.8857	High Similarity	NPD1918	Clinical (unspecified phase)
0.8806	High Similarity	NPD3476	Approved
0.8806	High Similarity	NPD3475	Approved
0.875	High Similarity	NPD4030	Approved
0.875	High Similarity	NPD4028	Approved
0.875	High Similarity	NPD4029	Approved
0.8652	High Similarity	NPD2006	Phase 2
0.8623	High Similarity	NPD1256	Approved
0.8623	High Similarity	NPD1255	Approved
0.8623	High Similarity	NPD1253	Approved
0.8623	High Similarity	NPD1254	Approved
0.8611	High Similarity	NPD2430	Phase 2
0.8611	High Similarity	NPD3100	Discontinued
0.8582	High Similarity	NPD1722	Approved
0.8562	High Similarity	NPD2837	Discontinued
0.8533	High Similarity	NPD3323	Discontinued
0.8521	High Similarity	NPD4637	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD5315	Discontinued
0.8456	Intermediate Similarity	NPD3654	Approved
0.8444	Intermediate Similarity	NPD991	Phase 2
0.8444	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD2072	Approved
0.844	Intermediate Similarity	NPD2075	Approved
0.844	Intermediate Similarity	NPD2068	Approved
0.844	Intermediate Similarity	NPD786	Approved
0.844	Intermediate Similarity	NPD2074	Approved
0.844	Intermediate Similarity	NPD2073	Approved
0.844	Intermediate Similarity	NPD2070	Approved
0.844	Intermediate Similarity	NPD2069	Approved
0.844	Intermediate Similarity	NPD2071	Approved
0.8429	Intermediate Similarity	NPD6554	Approved
0.8429	Intermediate Similarity	NPD45	Approved
0.8394	Intermediate Similarity	NPD715	Phase 3
0.8357	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1683	Approved
0.8345	Intermediate Similarity	NPD7469	Discontinued
0.8333	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD947	Approved
0.8299	Intermediate Similarity	NPD2172	Phase 1
0.8247	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD9583	Approved
0.8207	Intermediate Similarity	NPD4509	Discontinued
0.8188	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1994	Approved
0.8143	Intermediate Similarity	NPD1993	Approved
0.8143	Intermediate Similarity	NPD1995	Approved
0.8141	Intermediate Similarity	NPD3610	Approved
0.8141	Intermediate Similarity	NPD3609	Approved
0.8134	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD268	Approved
0.8134	Intermediate Similarity	NPD271	Approved
0.8133	Intermediate Similarity	NPD2165	Phase 1
0.8129	Intermediate Similarity	NPD2640	Approved
0.8129	Intermediate Similarity	NPD2641	Approved
0.8125	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2720	Phase 1
0.8117	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD9357	Approved
0.8079	Intermediate Similarity	NPD3112	Approved
0.8079	Intermediate Similarity	NPD3113	Approved
0.8079	Intermediate Similarity	NPD3114	Approved
0.8079	Intermediate Similarity	NPD3115	Approved
0.8077	Intermediate Similarity	NPD5436	Phase 1
0.805	Intermediate Similarity	NPD7111	Discontinued
0.8041	Intermediate Similarity	NPD4703	Approved
0.8041	Intermediate Similarity	NPD4702	Approved
0.8041	Intermediate Similarity	NPD1661	Suspended
0.8026	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4640	Approved
0.8013	Intermediate Similarity	NPD4639	Approved
0.8013	Intermediate Similarity	NPD4638	Approved
0.8013	Intermediate Similarity	NPD5862	Discovery
0.7987	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5254	Discontinued
0.7943	Intermediate Similarity	NPD1251	Discontinued
0.7937	Intermediate Similarity	NPD4181	Approved
0.7925	Intermediate Similarity	NPD5065	Approved
0.7922	Intermediate Similarity	NPD1403	Approved
0.7922	Intermediate Similarity	NPD1404	Approved
0.7922	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6497	Approved
0.7908	Intermediate Similarity	NPD4326	Phase 2
0.7898	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD976	Approved
0.7895	Intermediate Similarity	NPD977	Approved
0.7895	Intermediate Similarity	NPD975	Approved
0.7891	Intermediate Similarity	NPD4510	Discontinued
0.7881	Intermediate Similarity	NPD2882	Phase 1
0.7866	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD4824	Approved
0.7863	Intermediate Similarity	NPD4823	Approved
0.7843	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3813	Approved
0.7834	Intermediate Similarity	NPD2639	Approved
0.7834	Intermediate Similarity	NPD2642	Approved
0.7812	Intermediate Similarity	NPD4128	Approved
0.7786	Intermediate Similarity	NPD1598	Discontinued
0.7785	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2142	Approved
0.7778	Intermediate Similarity	NPD2141	Approved
0.7778	Intermediate Similarity	NPD2140	Approved
0.7771	Intermediate Similarity	NPD7394	Phase 2
0.777	Intermediate Similarity	NPD4047	Discontinued
0.7764	Intermediate Similarity	NPD4075	Phase 2
0.7763	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6158	Phase 2
0.7756	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6771	Discontinued
0.7752	Intermediate Similarity	NPD9098	Phase 3
0.7752	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7216	Approved
0.775	Intermediate Similarity	NPD7217	Approved
0.7748	Intermediate Similarity	NPD1183	Approved
0.7748	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5418	Discontinued
0.7742	Intermediate Similarity	NPD5255	Approved
0.7733	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2580	Discontinued
0.7716	Intermediate Similarity	NPD3506	Approved
0.7716	Intermediate Similarity	NPD3505	Approved
0.7712	Intermediate Similarity	NPD3339	Approved
0.7707	Intermediate Similarity	NPD3583	Phase 2
0.7704	Intermediate Similarity	NPD9392	Approved
0.7704	Intermediate Similarity	NPD9396	Approved
0.7702	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7564	Discontinued
0.7697	Intermediate Similarity	NPD4957	Phase 2
0.7697	Intermediate Similarity	NPD2466	Phase 3
0.7697	Intermediate Similarity	NPD2462	Phase 3
0.7697	Intermediate Similarity	NPD2465	Approved
0.7687	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2581	Approved
0.7677	Intermediate Similarity	NPD2582	Approved
0.7677	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4076	Approved
0.7669	Intermediate Similarity	NPD4079	Approved
0.7662	Intermediate Similarity	NPD6285	Phase 2
0.7658	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3262	Approved
0.7643	Intermediate Similarity	NPD5400	Approved
0.7643	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5105	Approved
0.7636	Intermediate Similarity	NPD5106	Approved
0.7607	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4902	Discontinued
0.7605	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD792	Discontinued
0.759	Intermediate Similarity	NPD5892	Approved
0.7582	Intermediate Similarity	NPD4463	Approved
0.7582	Intermediate Similarity	NPD4462	Approved
0.7578	Intermediate Similarity	NPD3117	Approved
0.7578	Intermediate Similarity	NPD3116	Approved
0.7574	Intermediate Similarity	NPD6281	Approved
0.7562	Intermediate Similarity	NPD5021	Discontinued
0.756	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3348	Phase 2
0.7545	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6299	Approved
0.7538	Intermediate Similarity	NPD6300	Approved
0.7533	Intermediate Similarity	NPD3717	Discontinued
0.7532	Intermediate Similarity	NPD4641	Discontinued
0.7516	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2150	Discontinued
0.75	Intermediate Similarity	NPD2144	Approved
0.75	Intermediate Similarity	NPD8122	Approved
0.75	Intermediate Similarity	NPD8123	Approved
0.75	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2896	Discontinued
0.75	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3799	Suspended
0.7485	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5671	Approved
0.7471	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2333	Discontinued
0.7439	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2771	Approved
0.7432	Intermediate Similarity	NPD1262	Discovery
0.7429	Intermediate Similarity	NPD5787	Discontinued
0.7424	Intermediate Similarity	NPD4116	Approved
0.741	Intermediate Similarity	NPD6595	Phase 3
0.7407	Intermediate Similarity	NPD4973	Approved
0.7407	Intermediate Similarity	NPD4184	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