NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	215.13
Volume:	240.192
LogP:	3.504
LogD:	3.075
LogS:	-3.435
# Rotatable Bonds:	3
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	2.459
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.553
MDCK Permeability:	1.0735865544120315e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9
Plasma Protein Binding (PPB):	91.0748062133789%
Volume Distribution (VD):	4.524
Pgp-substrate:	8.578839302062988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.518
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.361
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.454
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	11.888
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.694
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.72
Carcinogencity:	0.096
Eye Corrosion:	0.004
Eye Irritation:	0.704
Respiratory Toxicity:	0.169

Download Data

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

Natural Product: NPC313791

Natural Product ID:	NPC313791
*Common Name:**	6-Prenyltryptophol
IUPAC Name:	[6-(3-methylbut-2-enyl)-1H-indol-3-yl]methanol
Synonyms:	6-Prenyltryptophol
Standard InCHIKey:	REUSNXPKHWKIMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H17NO/c1-10(2)3-4-11-5-6-13-12(9-16)8-15-14(13)7-11/h3,5-8,15-16H,4,9H2,1-2H3
SMILES:	OCc1c[nH]c2c1ccc(c2)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL381959
PubChem CID:	44559649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO40579	Streptomyces sp. (BL-49-58-005)	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12828477]

☑ 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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	=	8460.0	nM	PMID[548284]

☑ 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 NPC313791 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	383
0.1-0.2	3526
0.2-0.3	14291
0.3-0.4	16265
0.4-0.5	3913
0.5-0.6	1990
0.6-0.7	1651
0.7-0.8	569
0.8-0.85	78
0.85-0.9	26
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC102423
0.9359	High Similarity	NPC131718
0.9051	High Similarity	NPC230869
0.8924	High Similarity	NPC469785
0.8868	High Similarity	NPC469762
0.8797	High Similarity	NPC25008
0.8797	High Similarity	NPC259644
0.8797	High Similarity	NPC469786
0.8797	High Similarity	NPC73952
0.8797	High Similarity	NPC469760
0.8797	High Similarity	NPC469765
0.8797	High Similarity	NPC469763
0.8765	High Similarity	NPC311276
0.8742	High Similarity	NPC211572
0.8742	High Similarity	NPC70922
0.8742	High Similarity	NPC80597
0.8742	High Similarity	NPC75540
0.8742	High Similarity	NPC212376
0.8671	High Similarity	NPC24678
0.8671	High Similarity	NPC105818
0.8654	High Similarity	NPC159856
0.8654	High Similarity	NPC314372
0.865	High Similarity	NPC40779
0.8647	High Similarity	NPC48938
0.8606	High Similarity	NPC201700
0.858	High Similarity	NPC176199
0.858	High Similarity	NPC215795
0.8526	High Similarity	NPC190296
0.8521	High Similarity	NPC151939
0.8497	Intermediate Similarity	NPC171171
0.8488	Intermediate Similarity	NPC204717
0.8457	Intermediate Similarity	NPC95783
0.8439	Intermediate Similarity	NPC314002
0.8434	Intermediate Similarity	NPC54988
0.843	Intermediate Similarity	NPC220765
0.8402	Intermediate Similarity	NPC37423
0.8402	Intermediate Similarity	NPC275305
0.8372	Intermediate Similarity	NPC71037
0.8364	Intermediate Similarity	NPC282231
0.8343	Intermediate Similarity	NPC46580
0.8323	Intermediate Similarity	NPC160105
0.8323	Intermediate Similarity	NPC474561
0.8323	Intermediate Similarity	NPC49954
0.8314	Intermediate Similarity	NPC300688
0.8304	Intermediate Similarity	NPC184964
0.8304	Intermediate Similarity	NPC68354
0.8303	Intermediate Similarity	NPC279918
0.8284	Intermediate Similarity	NPC470498
0.8258	Intermediate Similarity	NPC261195
0.8258	Intermediate Similarity	NPC29886
0.8242	Intermediate Similarity	NPC135141
0.8242	Intermediate Similarity	NPC92796
0.8239	Intermediate Similarity	NPC278434
0.8235	Intermediate Similarity	NPC314603
0.8232	Intermediate Similarity	NPC141353
0.8225	Intermediate Similarity	NPC194411
0.8222	Intermediate Similarity	NPC251090
0.8218	Intermediate Similarity	NPC469358
0.8217	Intermediate Similarity	NPC73767
0.8205	Intermediate Similarity	NPC84911
0.8199	Intermediate Similarity	NPC471957
0.8198	Intermediate Similarity	NPC96890
0.8171	Intermediate Similarity	NPC284678
0.8166	Intermediate Similarity	NPC63751
0.8165	Intermediate Similarity	NPC469761
0.8165	Intermediate Similarity	NPC469783
0.8165	Intermediate Similarity	NPC469768
0.8165	Intermediate Similarity	NPC469784
0.8165	Intermediate Similarity	NPC469779
0.8165	Intermediate Similarity	NPC469780
0.8165	Intermediate Similarity	NPC469767
0.8161	Intermediate Similarity	NPC233936
0.8156	Intermediate Similarity	NPC99666
0.8141	Intermediate Similarity	NPC96102
0.8125	Intermediate Similarity	NPC188387
0.8125	Intermediate Similarity	NPC163421
0.8114	Intermediate Similarity	NPC163055
0.8113	Intermediate Similarity	NPC469766
0.8111	Intermediate Similarity	NPC307963
0.8101	Intermediate Similarity	NPC110126
0.8095	Intermediate Similarity	NPC476118
0.8095	Intermediate Similarity	NPC194640
0.8092	Intermediate Similarity	NPC111275
0.8089	Intermediate Similarity	NPC105127
0.8079	Intermediate Similarity	NPC315555
0.8059	Intermediate Similarity	NPC78020
0.8045	Intermediate Similarity	NPC76748
0.8023	Intermediate Similarity	NPC34508
0.8022	Intermediate Similarity	NPC242209
0.8011	Intermediate Similarity	NPC106937
0.8	Intermediate Similarity	NPC138370
0.8	Intermediate Similarity	NPC92111
0.8	Intermediate Similarity	NPC49217
0.8	Intermediate Similarity	NPC82295
0.7989	Intermediate Similarity	NPC296527
0.7989	Intermediate Similarity	NPC248454
0.7978	Intermediate Similarity	NPC156704
0.7956	Intermediate Similarity	NPC324149
0.7953	Intermediate Similarity	NPC317430
0.7952	Intermediate Similarity	NPC470507
0.7944	Intermediate Similarity	NPC154339
0.7943	Intermediate Similarity	NPC213468
0.7943	Intermediate Similarity	NPC42979
0.7939	Intermediate Similarity	NPC216713
0.7937	Intermediate Similarity	NPC279081
0.7933	Intermediate Similarity	NPC317030
0.7931	Intermediate Similarity	NPC150048
0.7931	Intermediate Similarity	NPC224764
0.7931	Intermediate Similarity	NPC203754
0.7931	Intermediate Similarity	NPC267885
0.7921	Intermediate Similarity	NPC280290
0.7921	Intermediate Similarity	NPC15102
0.7914	Intermediate Similarity	NPC98715
0.7912	Intermediate Similarity	NPC267343
0.791	Intermediate Similarity	NPC19679
0.7903	Intermediate Similarity	NPC300183
0.7892	Intermediate Similarity	NPC200214
0.7886	Intermediate Similarity	NPC59269
0.788	Intermediate Similarity	NPC77555
0.7877	Intermediate Similarity	NPC474707
0.7874	Intermediate Similarity	NPC203468
0.7874	Intermediate Similarity	NPC149155
0.7874	Intermediate Similarity	NPC110500
0.7869	Intermediate Similarity	NPC133366
0.7857	Intermediate Similarity	NPC286427
0.7849	Intermediate Similarity	NPC470497
0.7845	Intermediate Similarity	NPC83111
0.7841	Intermediate Similarity	NPC270009
0.7841	Intermediate Similarity	NPC126709
0.7841	Intermediate Similarity	NPC248041
0.7833	Intermediate Similarity	NPC204565
0.7826	Intermediate Similarity	NPC230002
0.7826	Intermediate Similarity	NPC13880
0.7821	Intermediate Similarity	NPC476319
0.7818	Intermediate Similarity	NPC37548
0.7814	Intermediate Similarity	NPC474177
0.7811	Intermediate Similarity	NPC206819
0.7811	Intermediate Similarity	NPC318065
0.7811	Intermediate Similarity	NPC41257
0.7811	Intermediate Similarity	NPC56765
0.779	Intermediate Similarity	NPC173028
0.779	Intermediate Similarity	NPC32771
0.779	Intermediate Similarity	NPC65215
0.7789	Intermediate Similarity	NPC225821
0.7789	Intermediate Similarity	NPC46225
0.7789	Intermediate Similarity	NPC88008
0.7784	Intermediate Similarity	NPC229332
0.7784	Intermediate Similarity	NPC293472
0.7778	Intermediate Similarity	NPC90723
0.7778	Intermediate Similarity	NPC470500
0.7778	Intermediate Similarity	NPC470505
0.7772	Intermediate Similarity	NPC326634
0.7771	Intermediate Similarity	NPC53947
0.776	Intermediate Similarity	NPC5145
0.7754	Intermediate Similarity	NPC315491
0.7754	Intermediate Similarity	NPC45459
0.7754	Intermediate Similarity	NPC213308
0.7753	Intermediate Similarity	NPC192270
0.7753	Intermediate Similarity	NPC314394
0.7749	Intermediate Similarity	NPC258062
0.7749	Intermediate Similarity	NPC127677
0.7746	Intermediate Similarity	NPC154293
0.774	Intermediate Similarity	NPC72980
0.774	Intermediate Similarity	NPC55772
0.774	Intermediate Similarity	NPC283219
0.774	Intermediate Similarity	NPC472443
0.773	Intermediate Similarity	NPC205403
0.7714	Intermediate Similarity	NPC474409
0.7714	Intermediate Similarity	NPC472123
0.7711	Intermediate Similarity	NPC321911
0.7701	Intermediate Similarity	NPC32200
0.7697	Intermediate Similarity	NPC143872
0.7697	Intermediate Similarity	NPC288838
0.7692	Intermediate Similarity	NPC128751
0.7692	Intermediate Similarity	NPC285469
0.7684	Intermediate Similarity	NPC145885
0.7684	Intermediate Similarity	NPC14113
0.7684	Intermediate Similarity	NPC84827
0.7684	Intermediate Similarity	NPC475070
0.7683	Intermediate Similarity	NPC242556
0.768	Intermediate Similarity	NPC235684
0.768	Intermediate Similarity	NPC94752
0.767	Intermediate Similarity	NPC293216
0.767	Intermediate Similarity	NPC329688
0.767	Intermediate Similarity	NPC189812
0.7661	Intermediate Similarity	NPC44773
0.7661	Intermediate Similarity	NPC215584
0.7658	Intermediate Similarity	NPC256893
0.7657	Intermediate Similarity	NPC158129
0.7651	Intermediate Similarity	NPC469811
0.7651	Intermediate Similarity	NPC201380
0.7651	Intermediate Similarity	NPC179787
0.765	Intermediate Similarity	NPC469497
0.765	Intermediate Similarity	NPC106833
0.7647	Intermediate Similarity	NPC470499
0.7647	Intermediate Similarity	NPC131887
0.7647	Intermediate Similarity	NPC129721
0.7647	Intermediate Similarity	NPC473640
0.7634	Intermediate Similarity	NPC222018
0.7633	Intermediate Similarity	NPC38736

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 NPC313791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	673
0.2-0.3	834
0.3-0.4	1467
0.4-0.5	2731
0.5-0.6	2116
0.6-0.7	904
0.7-0.8	185
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8735	High Similarity	NPD5065	Approved
0.8494	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD4076	Approved
0.8363	Intermediate Similarity	NPD4079	Approved
0.8333	Intermediate Similarity	NPD1325	Approved
0.8333	Intermediate Similarity	NPD1326	Approved
0.8304	Intermediate Similarity	NPD3505	Approved
0.8304	Intermediate Similarity	NPD3506	Approved
0.8225	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD786	Approved
0.8141	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1592	Phase 3
0.8111	Intermediate Similarity	NPD1038	Approved
0.8111	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6595	Phase 3
0.8098	Intermediate Similarity	NPD4462	Approved
0.8098	Intermediate Similarity	NPD4463	Approved
0.8095	Intermediate Similarity	NPD5140	Approved
0.8095	Intermediate Similarity	NPD5138	Approved
0.8092	Intermediate Similarity	NPD2144	Approved
0.8011	Intermediate Similarity	NPD802	Phase 2
0.8	Intermediate Similarity	NPD1722	Approved
0.7979	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3038	Discontinued
0.7931	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7948	Phase 1
0.7874	Intermediate Similarity	NPD482	Approved
0.7866	Intermediate Similarity	NPD4702	Approved
0.7866	Intermediate Similarity	NPD4703	Approved
0.7861	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3404	Approved
0.7849	Intermediate Similarity	NPD4638	Approved
0.7849	Intermediate Similarity	NPD4640	Approved
0.7849	Intermediate Similarity	NPD4639	Approved
0.7845	Intermediate Similarity	NPD5117	Phase 2
0.7833	Intermediate Similarity	NPD8431	Approved
0.7818	Intermediate Similarity	NPD3100	Discontinued
0.7809	Intermediate Similarity	NPD2095	Phase 2
0.7809	Intermediate Similarity	NPD2094	Phase 2
0.7809	Intermediate Similarity	NPD2092	Phase 2
0.7809	Intermediate Similarity	NPD5596	Phase 2
0.7772	Intermediate Similarity	NPD8093	Discontinued
0.7771	Intermediate Similarity	NPD2172	Phase 1
0.7765	Intermediate Similarity	NPD2096	Phase 2
0.7765	Intermediate Similarity	NPD2091	Phase 2
0.7754	Intermediate Similarity	NPD484	Approved
0.7747	Intermediate Similarity	NPD6281	Approved
0.7732	Intermediate Similarity	NPD8094	Discontinued
0.7727	Intermediate Similarity	NPD2381	Approved
0.7727	Intermediate Similarity	NPD5100	Phase 3
0.7727	Intermediate Similarity	NPD2380	Approved
0.7727	Intermediate Similarity	NPD2382	Approved
0.7722	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5255	Approved
0.7696	Intermediate Similarity	NPD1392	Approved
0.7692	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4181	Approved
0.7684	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3323	Discontinued
0.767	Intermediate Similarity	NPD4128	Approved
0.7644	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5066	Phase 2
0.7629	Intermediate Similarity	NPD5067	Phase 2
0.7627	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2882	Phase 1
0.7619	Intermediate Similarity	NPD6158	Phase 2
0.7617	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD750	Phase 2
0.7606	Intermediate Similarity	NPD3825	Phase 3
0.7592	Intermediate Similarity	NPD5901	Discontinued
0.759	Intermediate Similarity	NPD3330	Phase 1
0.7582	Intermediate Similarity	NPD706	Phase 1
0.7576	Intermediate Similarity	NPD5254	Discontinued
0.7565	Intermediate Similarity	NPD2509	Approved
0.7565	Intermediate Similarity	NPD2510	Approved
0.7558	Intermediate Similarity	NPD1404	Approved
0.7558	Intermediate Similarity	NPD1403	Approved
0.7538	Intermediate Similarity	NPD7470	Discontinued
0.7529	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4075	Phase 2
0.7515	Intermediate Similarity	NPD3717	Discontinued
0.7514	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5612	Discontinued
0.7471	Intermediate Similarity	NPD2837	Discontinued
0.747	Intermediate Similarity	NPD3813	Approved
0.7459	Intermediate Similarity	NPD1043	Phase 3
0.7459	Intermediate Similarity	NPD3178	Discontinued
0.7458	Intermediate Similarity	NPD3609	Approved
0.7458	Intermediate Similarity	NPD3610	Approved
0.7446	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5021	Discontinued
0.7442	Intermediate Similarity	NPD2582	Approved
0.7442	Intermediate Similarity	NPD2581	Approved
0.7435	Intermediate Similarity	NPD4511	Phase 1
0.7432	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8272	Phase 2
0.7396	Intermediate Similarity	NPD6975	Discontinued
0.7386	Intermediate Similarity	NPD2639	Approved
0.7386	Intermediate Similarity	NPD2642	Approved
0.7385	Intermediate Similarity	NPD2187	Approved
0.7385	Intermediate Similarity	NPD2189	Approved
0.7385	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8072	Approved
0.7351	Intermediate Similarity	NPD2383	Phase 1
0.7351	Intermediate Similarity	NPD3961	Discontinued
0.7345	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2641	Approved
0.7345	Intermediate Similarity	NPD2640	Approved
0.7345	Intermediate Similarity	NPD2844	Phase 3
0.7341	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1768	Approved
0.7326	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5913	Phase 3
0.7326	Intermediate Similarity	NPD4699	Discontinued
0.7317	Intermediate Similarity	NPD1262	Discovery
0.7306	Intermediate Similarity	NPD3928	Approved
0.7306	Intermediate Similarity	NPD3931	Approved
0.7305	Intermediate Similarity	NPD3525	Discontinued
0.7302	Intermediate Similarity	NPD4999	Phase 3
0.7302	Intermediate Similarity	NPD4998	Phase 3
0.73	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3003	Approved
0.7278	Intermediate Similarity	NPD6492	Phase 2
0.7268	Intermediate Similarity	NPD7867	Phase 1
0.7267	Intermediate Similarity	NPD3475	Approved
0.7267	Intermediate Similarity	NPD3476	Approved
0.7264	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5862	Discovery
0.7247	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2175	Phase 3
0.724	Intermediate Similarity	NPD2177	Approved
0.724	Intermediate Similarity	NPD2176	Approved
0.7235	Intermediate Similarity	NPD1661	Suspended
0.7232	Intermediate Similarity	NPD925	Approved
0.7232	Intermediate Similarity	NPD926	Approved
0.7231	Intermediate Similarity	NPD5426	Phase 3
0.7231	Intermediate Similarity	NPD4795	Phase 2
0.7228	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8073	Approved
0.7214	Intermediate Similarity	NPD3394	Approved
0.7214	Intermediate Similarity	NPD3389	Approved
0.7214	Intermediate Similarity	NPD3393	Approved
0.7213	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4612	Discontinued
0.7204	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1739	Approved
0.7202	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1740	Approved
0.72	Intermediate Similarity	NPD2615	Phase 3
0.72	Intermediate Similarity	NPD2616	Phase 3
0.72	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2127	Suspended
0.7196	Intermediate Similarity	NPD4615	Phase 2
0.7194	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7957	Phase 1
0.7191	Intermediate Similarity	NPD424	Approved
0.7191	Intermediate Similarity	NPD425	Approved
0.719	Intermediate Similarity	NPD7558	Phase 2
0.7188	Intermediate Similarity	NPD9080	Approved
0.7188	Intermediate Similarity	NPD9284	Approved
0.7186	Intermediate Similarity	NPD5475	Discontinued
0.7184	Intermediate Similarity	NPD2580	Discontinued
0.7182	Intermediate Similarity	NPD2928	Phase 2
0.7182	Intermediate Similarity	NPD9690	Approved
0.7179	Intermediate Similarity	NPD4886	Phase 2
0.7167	Intermediate Similarity	NPD3117	Approved
0.7167	Intermediate Similarity	NPD3116	Approved
0.7166	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD112	Approved
0.7159	Intermediate Similarity	NPD9705	Discontinued
0.7158	Intermediate Similarity	NPD5428	Discontinued
0.7157	Intermediate Similarity	NPD4865	Approved
0.7151	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3082	Discontinued
0.7151	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1315	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5081	Phase 1
0.7143	Intermediate Similarity	NPD5082	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5003	Discontinued
0.7135	Intermediate Similarity	NPD6664	Approved
0.7129	Intermediate Similarity	NPD6957	Approved
0.7129	Intermediate Similarity	NPD6958	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