NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	211.1
Volume:	234.919
LogP:	3.232
LogD:	3.205
LogS:	-4.166
# Rotatable Bonds:	3
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.844
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.913
MDCK Permeability:	1.0065166861750185e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.769
Plasma Protein Binding (PPB):	91.65950775146484%
Volume Distribution (VD):	1.052
Pgp-substrate:	5.955909729003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.8
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.484
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	3.621
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.951
Carcinogencity:	0.564
Eye Corrosion:	0.881
Eye Irritation:	0.995
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC293216

Natural Product ID:	NPC293216
*Common Name:**	Indiacen A
IUPAC Name:	4-[(1E)-3-methylbuta-1,3-dienyl]-1H-indole-3-carbaldehyde
Synonyms:	Indiacen A
Standard InCHIKey:	AXOXRKLGTGXWJN-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C14H13NO/c1-10(2)6-7-11-4-3-5-13-14(11)12(9-16)8-15-13/h3-9,15H,1H2,2H3/b7-6+
SMILES:	C=C(C)/C=C/c1cccc2c1c(c[nH]2)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152638
PubChem CID:	71451259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO33314	sandaracinus amylolyticus	Species	Sandaracinaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23035772]

☑ 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
MIC	8

Activity Type	# Activity
NON-MOLECULAR	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	16.6	ug.mL-1	PMID[539125]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	8.3	ug.mL-1	PMID[539125]
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	=	16.6	ug.mL-1	PMID[539125]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	33.0	ug.mL-1	PMID[539125]
NPT2631	Organism	Chromobacterium violaceum	Chromobacterium violaceum	MIC	=	16.6	ug.mL-1	PMID[539125]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.6	ug.mL-1	PMID[539125]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	16.6	ug.mL-1	PMID[539125]

☑ 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 NPC293216 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	532
0.1-0.2	5605
0.2-0.3	16582
0.3-0.4	13945
0.4-0.5	2230
0.5-0.6	1942
0.6-0.7	1331
0.7-0.8	486
0.8-0.85	34
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC470677
0.9615	High Similarity	NPC42372
0.9	High Similarity	NPC242116
0.8876	High Similarity	NPC110158
0.8834	High Similarity	NPC114637
0.8706	High Similarity	NPC102755
0.869	High Similarity	NPC284775
0.8547	High Similarity	NPC477003
0.8514	High Similarity	NPC154339
0.8475	Intermediate Similarity	NPC267343
0.8466	Intermediate Similarity	NPC138370
0.843	Intermediate Similarity	NPC191415
0.8295	Intermediate Similarity	NPC278434
0.8263	Intermediate Similarity	NPC265100
0.8258	Intermediate Similarity	NPC476460
0.8242	Intermediate Similarity	NPC76982
0.8239	Intermediate Similarity	NPC190296
0.8205	Intermediate Similarity	NPC29886
0.8205	Intermediate Similarity	NPC261195
0.8167	Intermediate Similarity	NPC326422
0.8167	Intermediate Similarity	NPC304203
0.8153	Intermediate Similarity	NPC84911
0.8137	Intermediate Similarity	NPC314372
0.8107	Intermediate Similarity	NPC115232
0.8095	Intermediate Similarity	NPC214106
0.8089	Intermediate Similarity	NPC96102
0.805	Intermediate Similarity	NPC110126
0.805	Intermediate Similarity	NPC73767
0.8038	Intermediate Similarity	NPC105127
0.8025	Intermediate Similarity	NPC159856
0.8012	Intermediate Similarity	NPC78020
0.8	Intermediate Similarity	NPC469779
0.8	Intermediate Similarity	NPC469783
0.8	Intermediate Similarity	NPC469768
0.8	Intermediate Similarity	NPC469784
0.8	Intermediate Similarity	NPC469767
0.8	Intermediate Similarity	NPC469761
0.8	Intermediate Similarity	NPC469780
0.7955	Intermediate Similarity	NPC88110
0.795	Intermediate Similarity	NPC469766
0.7949	Intermediate Similarity	NPC82295
0.7946	Intermediate Similarity	NPC477004
0.7943	Intermediate Similarity	NPC111275
0.7939	Intermediate Similarity	NPC105818
0.7939	Intermediate Similarity	NPC24678
0.7937	Intermediate Similarity	NPC183777
0.7935	Intermediate Similarity	NPC167710
0.7927	Intermediate Similarity	NPC471957
0.7898	Intermediate Similarity	NPC55772
0.7898	Intermediate Similarity	NPC213468
0.7895	Intermediate Similarity	NPC171787
0.7888	Intermediate Similarity	NPC279081
0.7886	Intermediate Similarity	NPC267885
0.7884	Intermediate Similarity	NPC82053
0.7877	Intermediate Similarity	NPC282103
0.7857	Intermediate Similarity	NPC469785
0.7844	Intermediate Similarity	NPC25008
0.7844	Intermediate Similarity	NPC200214
0.7844	Intermediate Similarity	NPC469763
0.7844	Intermediate Similarity	NPC469765
0.7844	Intermediate Similarity	NPC259644
0.7844	Intermediate Similarity	NPC469760
0.7844	Intermediate Similarity	NPC73952
0.7844	Intermediate Similarity	NPC469786
0.7841	Intermediate Similarity	NPC14113
0.7841	Intermediate Similarity	NPC145885
0.7841	Intermediate Similarity	NPC84827
0.7829	Intermediate Similarity	NPC203468
0.7829	Intermediate Similarity	NPC275305
0.7829	Intermediate Similarity	NPC110500
0.7829	Intermediate Similarity	NPC149155
0.7829	Intermediate Similarity	NPC37423
0.7814	Intermediate Similarity	NPC47190
0.7811	Intermediate Similarity	NPC286427
0.7811	Intermediate Similarity	NPC469762
0.7803	Intermediate Similarity	NPC70949
0.7798	Intermediate Similarity	NPC211572
0.7798	Intermediate Similarity	NPC80597
0.7798	Intermediate Similarity	NPC75540
0.7798	Intermediate Similarity	NPC70922
0.7798	Intermediate Similarity	NPC212376
0.7797	Intermediate Similarity	NPC248041
0.7797	Intermediate Similarity	NPC11126
0.7797	Intermediate Similarity	NPC126709
0.7778	Intermediate Similarity	NPC230002
0.7778	Intermediate Similarity	NPC317701
0.7778	Intermediate Similarity	NPC133003
0.7765	Intermediate Similarity	NPC80681
0.7765	Intermediate Similarity	NPC56765
0.7765	Intermediate Similarity	NPC230869
0.7765	Intermediate Similarity	NPC206819
0.7765	Intermediate Similarity	NPC474492
0.7765	Intermediate Similarity	NPC470205
0.7765	Intermediate Similarity	NPC41257
0.7765	Intermediate Similarity	NPC318065
0.7759	Intermediate Similarity	NPC194411
0.7754	Intermediate Similarity	NPC237414
0.774	Intermediate Similarity	NPC68354
0.7733	Intermediate Similarity	NPC40779
0.7733	Intermediate Similarity	NPC311276
0.773	Intermediate Similarity	NPC157828
0.773	Intermediate Similarity	NPC195239
0.7719	Intermediate Similarity	NPC100104
0.7719	Intermediate Similarity	NPC470680
0.7709	Intermediate Similarity	NPC243381
0.7709	Intermediate Similarity	NPC275292
0.7705	Intermediate Similarity	NPC83111
0.7701	Intermediate Similarity	NPC201700
0.7697	Intermediate Similarity	NPC176199
0.7697	Intermediate Similarity	NPC276540
0.7697	Intermediate Similarity	NPC233050
0.7697	Intermediate Similarity	NPC215795
0.7697	Intermediate Similarity	NPC283219
0.7688	Intermediate Similarity	NPC11445
0.7688	Intermediate Similarity	NPC23215
0.7684	Intermediate Similarity	NPC151635
0.768	Intermediate Similarity	NPC99939
0.768	Intermediate Similarity	NPC308931
0.7679	Intermediate Similarity	NPC216713
0.767	Intermediate Similarity	NPC313791
0.7665	Intermediate Similarity	NPC321911
0.7654	Intermediate Similarity	NPC477042
0.7651	Intermediate Similarity	NPC288838
0.7651	Intermediate Similarity	NPC143872
0.7641	Intermediate Similarity	NPC219087
0.764	Intermediate Similarity	NPC473380
0.764	Intermediate Similarity	NPC240088
0.7637	Intermediate Similarity	NPC315555
0.7637	Intermediate Similarity	NPC135601
0.7637	Intermediate Similarity	NPC141612
0.7637	Intermediate Similarity	NPC17273
0.7634	Intermediate Similarity	NPC202812
0.7633	Intermediate Similarity	NPC251391
0.763	Intermediate Similarity	NPC102423
0.763	Intermediate Similarity	NPC90723
0.7627	Intermediate Similarity	NPC469529
0.7624	Intermediate Similarity	NPC228835
0.7624	Intermediate Similarity	NPC21429
0.7619	Intermediate Similarity	NPC53947
0.7616	Intermediate Similarity	NPC44773
0.7616	Intermediate Similarity	NPC215584
0.7611	Intermediate Similarity	NPC71037
0.7609	Intermediate Similarity	NPC324091
0.7605	Intermediate Similarity	NPC469811
0.7605	Intermediate Similarity	NPC201380
0.7605	Intermediate Similarity	NPC179787
0.7598	Intermediate Similarity	NPC265710
0.7594	Intermediate Similarity	NPC102592
0.7594	Intermediate Similarity	NPC79356
0.7592	Intermediate Similarity	NPC98715
0.759	Intermediate Similarity	NPC467188
0.7586	Intermediate Similarity	NPC233380
0.7581	Intermediate Similarity	NPC88315
0.7574	Intermediate Similarity	NPC470823
0.7574	Intermediate Similarity	NPC70406
0.7572	Intermediate Similarity	NPC282231
0.7571	Intermediate Similarity	NPC252572
0.7566	Intermediate Similarity	NPC472297
0.7566	Intermediate Similarity	NPC472296
0.7566	Intermediate Similarity	NPC74413
0.7558	Intermediate Similarity	NPC135141
0.7558	Intermediate Similarity	NPC92796
0.7557	Intermediate Similarity	NPC471943
0.7556	Intermediate Similarity	NPC73994
0.7556	Intermediate Similarity	NPC16659
0.7553	Intermediate Similarity	NPC227582
0.7545	Intermediate Similarity	NPC63545
0.7543	Intermediate Similarity	NPC54988
0.7542	Intermediate Similarity	NPC237188
0.7541	Intermediate Similarity	NPC235684
0.7538	Intermediate Similarity	NPC123839
0.7529	Intermediate Similarity	NPC141926
0.7529	Intermediate Similarity	NPC271797
0.7529	Intermediate Similarity	NPC21174
0.7527	Intermediate Similarity	NPC467063
0.7526	Intermediate Similarity	NPC266249
0.7526	Intermediate Similarity	NPC116555
0.7515	Intermediate Similarity	NPC101130
0.7515	Intermediate Similarity	NPC58268
0.7515	Intermediate Similarity	NPC129412
0.7515	Intermediate Similarity	NPC114033
0.7515	Intermediate Similarity	NPC471655
0.7514	Intermediate Similarity	NPC279918
0.7514	Intermediate Similarity	NPC131718
0.7514	Intermediate Similarity	NPC470498
0.75	Intermediate Similarity	NPC105811
0.7487	Intermediate Similarity	NPC300183
0.7486	Intermediate Similarity	NPC280290
0.7485	Intermediate Similarity	NPC209362
0.7485	Intermediate Similarity	NPC34844
0.7485	Intermediate Similarity	NPC470440
0.7474	Intermediate Similarity	NPC225821
0.7474	Intermediate Similarity	NPC46225
0.7473	Intermediate Similarity	NPC469358
0.7469	Intermediate Similarity	NPC291517
0.7462	Intermediate Similarity	NPC470702
0.7462	Intermediate Similarity	NPC6865
0.7462	Intermediate Similarity	NPC153980
0.7462	Intermediate Similarity	NPC473218
0.7456	Intermediate Similarity	NPC123906

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 NPC293216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	742
0.2-0.3	950
0.3-0.4	2250
0.4-0.5	2252
0.5-0.6	1844
0.6-0.7	703
0.7-0.8	116
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD3607	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD3318	Approved
0.8068	Intermediate Similarity	NPD3320	Approved
0.8068	Intermediate Similarity	NPD3319	Phase 1
0.805	Intermediate Similarity	NPD786	Approved
0.7989	Intermediate Similarity	NPD4075	Phase 2
0.7968	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD2479	Phase 3
0.7955	Intermediate Similarity	NPD2481	Approved
0.7903	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2509	Approved
0.7895	Intermediate Similarity	NPD2510	Approved
0.7886	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1722	Approved
0.7829	Intermediate Similarity	NPD482	Approved
0.7812	Intermediate Similarity	NPD4051	Discontinued
0.7789	Intermediate Similarity	NPD2008	Discontinued
0.7772	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3505	Approved
0.774	Intermediate Similarity	NPD3506	Approved
0.7717	Intermediate Similarity	NPD4922	Phase 2
0.7697	Intermediate Similarity	NPD4079	Approved
0.7697	Intermediate Similarity	NPD4076	Approved
0.7688	Intermediate Similarity	NPD4848	Phase 1
0.7665	Intermediate Similarity	NPD3100	Discontinued
0.7647	Intermediate Similarity	NPD6664	Approved
0.7641	Intermediate Similarity	NPD2411	Approved
0.763	Intermediate Similarity	NPD3323	Discontinued
0.7624	Intermediate Similarity	NPD2096	Phase 2
0.7624	Intermediate Similarity	NPD2091	Phase 2
0.7624	Intermediate Similarity	NPD7564	Discontinued
0.7619	Intermediate Similarity	NPD2172	Phase 1
0.76	Intermediate Similarity	NPD1343	Approved
0.7571	Intermediate Similarity	NPD750	Phase 2
0.7569	Intermediate Similarity	NPD2095	Phase 2
0.7569	Intermediate Similarity	NPD2094	Phase 2
0.7569	Intermediate Similarity	NPD2092	Phase 2
0.7569	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5473	Discontinued
0.7528	Intermediate Similarity	NPD4128	Approved
0.7525	Intermediate Similarity	NPD3389	Approved
0.7525	Intermediate Similarity	NPD3394	Approved
0.7525	Intermediate Similarity	NPD3393	Approved
0.75	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1270	Approved
0.7447	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4181	Approved
0.7429	Intermediate Similarity	NPD3583	Phase 2
0.7425	Intermediate Similarity	NPD5254	Discontinued
0.7416	Intermediate Similarity	NPD3610	Approved
0.7416	Intermediate Similarity	NPD3609	Approved
0.7414	Intermediate Similarity	NPD1403	Approved
0.7414	Intermediate Similarity	NPD1404	Approved
0.7405	Intermediate Similarity	NPD3961	Discontinued
0.7394	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7455	Approved
0.7374	Intermediate Similarity	NPD7454	Approved
0.7371	Intermediate Similarity	NPD5901	Discontinued
0.736	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7619	Phase 3
0.7354	Intermediate Similarity	NPD7618	Phase 3
0.7349	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2144	Approved
0.7347	Intermediate Similarity	NPD2443	Approved
0.7347	Intermediate Similarity	NPD2442	Approved
0.7337	Intermediate Similarity	NPD5888	Phase 2
0.7326	Intermediate Similarity	NPD2837	Discontinued
0.7323	Intermediate Similarity	NPD5475	Discontinued
0.7322	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2639	Approved
0.7247	Intermediate Similarity	NPD2642	Approved
0.7231	Intermediate Similarity	NPD6176	Phase 1
0.7228	Intermediate Similarity	NPD3038	Discontinued
0.7228	Intermediate Similarity	NPD3178	Discontinued
0.7216	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD460	Discontinued
0.7209	Intermediate Similarity	NPD4463	Approved
0.7209	Intermediate Similarity	NPD4462	Approved
0.7207	Intermediate Similarity	NPD2640	Approved
0.7207	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4640	Approved
0.7207	Intermediate Similarity	NPD4639	Approved
0.7207	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2641	Approved
0.7207	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4638	Approved
0.7194	Intermediate Similarity	NPD3947	Discontinued
0.7175	Intermediate Similarity	NPD5400	Approved
0.7174	Intermediate Similarity	NPD6595	Phase 3
0.7169	Intermediate Similarity	NPD201	Phase 2
0.7169	Intermediate Similarity	NPD200	Phase 2
0.7166	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6479	Discontinued
0.7159	Intermediate Similarity	NPD2213	Approved
0.7159	Intermediate Similarity	NPD2214	Approved
0.7157	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1982	Phase 1
0.7143	Intermediate Similarity	NPD5065	Approved
0.7143	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2408	Discontinued
0.7134	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4988	Discontinued
0.7122	Intermediate Similarity	NPD6242	Discontinued
0.7111	Intermediate Similarity	NPD5021	Discontinued
0.7107	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6987	Phase 1
0.7105	Intermediate Similarity	NPD2336	Approved
0.7104	Intermediate Similarity	NPD3238	Discontinued
0.7095	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2879	Approved
0.7092	Intermediate Similarity	NPD2881	Approved
0.7074	Intermediate Similarity	NPD6217	Discontinued
0.7071	Intermediate Similarity	NPD7010	Phase 3
0.7071	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1262	Discovery
0.7065	Intermediate Similarity	NPD2753	Discontinued
0.7059	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1600	Suspended
0.7048	Intermediate Similarity	NPD272	Approved
0.7045	Intermediate Similarity	NPD2580	Discontinued
0.7041	Intermediate Similarity	NPD9599	Approved
0.7037	Intermediate Similarity	NPD991	Phase 2
0.7037	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8431	Approved
0.7035	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5426	Phase 3
0.7015	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5198	Approved
0.699	Remote Similarity	NPD5199	Approved
0.699	Remote Similarity	NPD484	Approved
0.6989	Remote Similarity	NPD976	Approved
0.6989	Remote Similarity	NPD975	Approved
0.6989	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD977	Approved
0.697	Remote Similarity	NPD8072	Approved
0.6966	Remote Similarity	NPD1630	Approved
0.6963	Remote Similarity	NPD4499	Approved
0.6959	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2307	Discontinued
0.6957	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3654	Approved
0.695	Remote Similarity	NPD3905	Phase 3
0.695	Remote Similarity	NPD1506	Discontinued
0.6947	Remote Similarity	NPD4948	Discontinued
0.6947	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8093	Discontinued
0.6936	Remote Similarity	NPD1683	Approved
0.6931	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2880	Discontinued
0.6919	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6459	Phase 2
0.6912	Remote Similarity	NPD8094	Discontinued
0.6911	Remote Similarity	NPD7175	Phase 1
0.6909	Remote Similarity	NPD3475	Approved
0.6909	Remote Similarity	NPD3476	Approved
0.6906	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3927	Phase 2
0.6898	Remote Similarity	NPD1618	Phase 2
0.6897	Remote Similarity	NPD4547	Phase 3
0.6897	Remote Similarity	NPD6152	Phase 1
0.6897	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7470	Discontinued
0.6895	Remote Similarity	NPD5809	Phase 3
0.6893	Remote Similarity	NPD2061	Approved
0.6889	Remote Similarity	NPD5315	Discontinued
0.6886	Remote Similarity	NPD4029	Approved
0.6886	Remote Similarity	NPD4028	Approved
0.6886	Remote Similarity	NPD4030	Approved
0.6879	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1248	Discontinued
0.6868	Remote Similarity	NPD6446	Discontinued
0.6865	Remote Similarity	NPD4883	Approved
0.6863	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD1895	Discontinued
0.686	Remote Similarity	NPD2006	Phase 2
0.6857	Remote Similarity	NPD2430	Phase 2
0.6854	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1631	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