NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.11
Volume:	201.937
LogP:	1.07
LogD:	0.733
LogS:	-1.794
# Rotatable Bonds:	3
TPSA:	48.05
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	2.16
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	4.073620857525384e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.504
Plasma Protein Binding (PPB):	18.782997131347656%
Volume Distribution (VD):	2.296
Pgp-substrate:	72.56065368652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.626
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	8.502
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.927
Carcinogencity:	0.035
Eye Corrosion:	0.011
Eye Irritation:	0.055
Respiratory Toxicity:	0.674

Download Data

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

Natural Product: NPC204717

Natural Product ID:	NPC204717
*Common Name:**	3-[2-(Methylamino)Ethyl]-1H-Indol-5-Ol
IUPAC Name:	3-[2-(methylamino)ethyl]-1H-indol-5-ol
Synonyms:
Standard InCHIKey:	ASUSBMNYRHGZIG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3
SMILES:	CNCCc1c[nH]c2ccc(cc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL277362
PubChem CID:	150885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives [CHEMONTID:0001637] Serotonins

*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
AC50	1
Ki	5
Potency	11

Activity Type	# Activity
Individual Protein	14
Others	1
Protein Family	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT288	Individual Protein	Serotonin 1a (5-HT1a) receptor	Rattus norvegicus	Ki	=	5.0	nM	PMID[524804]
NPT289	Individual Protein	Serotonin 1b (5-HT1b) receptor	Rattus norvegicus	Ki	=	45.0	nM	PMID[524804]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	=	280.0	nM	PMID[524804]
NPT288	Individual Protein	Serotonin 1a (5-HT1a) receptor	Rattus norvegicus	Ki	=	4.898	nM	PMID[524805]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[524806]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	25059.4	nM	PMID[524806]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	39810.7	nM	PMID[524807]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Potency	n.a.	1835.5	nM	PMID[524808]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[524808]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[524808]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	39810.72	nM	PMID[524807]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	7519.3	nM	PMID[524808]
NPT104	Individual Protein	Cerebroside-sulfatase	Homo sapiens	Potency	n.a.	13459.1	nM	PMID[524808]
NPT1777	Protein Family	Serotonin 2 (5-HT2) receptor	Rattus norvegicus	Ki	=	180.0	nM	PMID[524804]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[524806]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[524808]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[524808]

☑ 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 NPC204717 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	573
0.1-0.2	5556
0.2-0.3	11805
0.3-0.4	13759
0.4-0.5	6036
0.5-0.6	2570
0.6-0.7	1640
0.7-0.8	644
0.8-0.85	70
0.85-0.9	25
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC220765
0.9939	High Similarity	NPC314002
0.9879	High Similarity	NPC171171
0.9693	High Similarity	NPC184964
0.9474	High Similarity	NPC99666
0.9257	High Similarity	NPC77555
0.9257	High Similarity	NPC156704
0.924	High Similarity	NPC46580
0.9195	High Similarity	NPC307963
0.9186	High Similarity	NPC296527
0.9133	High Similarity	NPC76748
0.9101	High Similarity	NPC45459
0.9101	High Similarity	NPC315491
0.9091	High Similarity	NPC251090
0.908	High Similarity	NPC92111
0.9075	High Similarity	NPC32771
0.8994	High Similarity	NPC213308
0.8927	High Similarity	NPC326634
0.8902	High Similarity	NPC131718
0.8901	High Similarity	NPC475070
0.8882	High Similarity	NPC96890
0.8876	High Similarity	NPC222018
0.883	High Similarity	NPC88363
0.8771	High Similarity	NPC242209
0.8703	High Similarity	NPC88008
0.8683	High Similarity	NPC102423
0.8626	High Similarity	NPC476167
0.8624	High Similarity	NPC266931
0.8613	High Similarity	NPC72980
0.8603	High Similarity	NPC324149
0.8579	High Similarity	NPC176538
0.8571	High Similarity	NPC192315
0.8571	High Similarity	NPC316981
0.8564	High Similarity	NPC5145
0.8556	High Similarity	NPC106937
0.8556	High Similarity	NPC171787
0.8526	High Similarity	NPC477610
0.8503	High Similarity	NPC230869
0.8488	Intermediate Similarity	NPC313791
0.8474	Intermediate Similarity	NPC219087
0.8466	Intermediate Similarity	NPC176127
0.8436	Intermediate Similarity	NPC246700
0.8436	Intermediate Similarity	NPC128751
0.8407	Intermediate Similarity	NPC276517
0.8402	Intermediate Similarity	NPC282231
0.8394	Intermediate Similarity	NPC476041
0.8394	Intermediate Similarity	NPC304926
0.8389	Intermediate Similarity	NPC469497
0.8389	Intermediate Similarity	NPC106833
0.8382	Intermediate Similarity	NPC474409
0.8378	Intermediate Similarity	NPC249040
0.8373	Intermediate Similarity	NPC25008
0.8373	Intermediate Similarity	NPC469763
0.8373	Intermediate Similarity	NPC259644
0.8373	Intermediate Similarity	NPC469765
0.8373	Intermediate Similarity	NPC73952
0.8373	Intermediate Similarity	NPC469786
0.8373	Intermediate Similarity	NPC469760
0.8361	Intermediate Similarity	NPC13880
0.836	Intermediate Similarity	NPC476465
0.8351	Intermediate Similarity	NPC477609
0.8344	Intermediate Similarity	NPC159856
0.8343	Intermediate Similarity	NPC279918
0.8342	Intermediate Similarity	NPC476098
0.8323	Intermediate Similarity	NPC211572
0.8323	Intermediate Similarity	NPC80597
0.8323	Intermediate Similarity	NPC212376
0.8323	Intermediate Similarity	NPC75540
0.8323	Intermediate Similarity	NPC70922
0.8308	Intermediate Similarity	NPC74360
0.8295	Intermediate Similarity	NPC42979
0.8286	Intermediate Similarity	NPC224764
0.8265	Intermediate Similarity	NPC276657
0.8256	Intermediate Similarity	NPC474561
0.8256	Intermediate Similarity	NPC49954
0.8256	Intermediate Similarity	NPC160105
0.8253	Intermediate Similarity	NPC105818
0.8253	Intermediate Similarity	NPC24678
0.8246	Intermediate Similarity	NPC311276
0.8232	Intermediate Similarity	NPC314372
0.8221	Intermediate Similarity	NPC190296
0.822	Intermediate Similarity	NPC476116
0.8191	Intermediate Similarity	NPC211813
0.8166	Intermediate Similarity	NPC469785
0.8161	Intermediate Similarity	NPC314940
0.8161	Intermediate Similarity	NPC473764
0.8158	Intermediate Similarity	NPC477113
0.8156	Intermediate Similarity	NPC212535
0.815	Intermediate Similarity	NPC54988
0.8141	Intermediate Similarity	NPC130570
0.8135	Intermediate Similarity	NPC208284
0.8118	Intermediate Similarity	NPC153042
0.8118	Intermediate Similarity	NPC469762
0.8115	Intermediate Similarity	NPC270918
0.8105	Intermediate Similarity	NPC470500
0.8103	Intermediate Similarity	NPC63751
0.81	Intermediate Similarity	NPC245348
0.8093	Intermediate Similarity	NPC128084
0.8073	Intermediate Similarity	NPC477111
0.8068	Intermediate Similarity	NPC314603
0.8066	Intermediate Similarity	NPC188387
0.8066	Intermediate Similarity	NPC94943
0.8066	Intermediate Similarity	NPC163421
0.8063	Intermediate Similarity	NPC476124
0.8063	Intermediate Similarity	NPC476121
0.8059	Intermediate Similarity	NPC141353
0.8056	Intermediate Similarity	NPC48938
0.8042	Intermediate Similarity	NPC232727
0.8041	Intermediate Similarity	NPC246518
0.8035	Intermediate Similarity	NPC194640
0.8021	Intermediate Similarity	NPC183777
0.8011	Intermediate Similarity	NPC190007
0.8	Intermediate Similarity	NPC78020
0.799	Intermediate Similarity	NPC11464
0.7989	Intermediate Similarity	NPC121772
0.798	Intermediate Similarity	NPC264285
0.798	Intermediate Similarity	NPC477608
0.798	Intermediate Similarity	NPC477607
0.7978	Intermediate Similarity	NPC267885
0.797	Intermediate Similarity	NPC60006
0.7958	Intermediate Similarity	NPC245816
0.7958	Intermediate Similarity	NPC223427
0.7958	Intermediate Similarity	NPC476138
0.7957	Intermediate Similarity	NPC329541
0.794	Intermediate Similarity	NPC213530
0.794	Intermediate Similarity	NPC193267
0.7938	Intermediate Similarity	NPC80596
0.7933	Intermediate Similarity	NPC248454
0.7933	Intermediate Similarity	NPC111275
0.7931	Intermediate Similarity	NPC40779
0.7931	Intermediate Similarity	NPC6215
0.7921	Intermediate Similarity	NPC203468
0.7921	Intermediate Similarity	NPC149155
0.7921	Intermediate Similarity	NPC110500
0.7917	Intermediate Similarity	NPC285558
0.7917	Intermediate Similarity	NPC471957
0.7914	Intermediate Similarity	NPC84911
0.7912	Intermediate Similarity	NPC84478
0.791	Intermediate Similarity	NPC252590
0.7906	Intermediate Similarity	NPC135887
0.7906	Intermediate Similarity	NPC199277
0.7906	Intermediate Similarity	NPC470678
0.7898	Intermediate Similarity	NPC201700
0.7895	Intermediate Similarity	NPC19872
0.7895	Intermediate Similarity	NPC329793
0.7895	Intermediate Similarity	NPC315957
0.7889	Intermediate Similarity	NPC248041
0.7889	Intermediate Similarity	NPC126709
0.7884	Intermediate Similarity	NPC306376
0.7879	Intermediate Similarity	NPC8022
0.7879	Intermediate Similarity	NPC470799
0.7879	Intermediate Similarity	NPC477110
0.7864	Intermediate Similarity	NPC207686
0.7861	Intermediate Similarity	NPC92796
0.7861	Intermediate Similarity	NPC135141
0.7861	Intermediate Similarity	NPC473317
0.7857	Intermediate Similarity	NPC469358
0.7853	Intermediate Similarity	NPC29886
0.7853	Intermediate Similarity	NPC96102
0.7853	Intermediate Similarity	NPC261195
0.7833	Intermediate Similarity	NPC151939
0.7833	Intermediate Similarity	NPC59269
0.7826	Intermediate Similarity	NPC315555
0.7818	Intermediate Similarity	NPC110126
0.7818	Intermediate Similarity	NPC73767
0.7809	Intermediate Similarity	NPC470498
0.7805	Intermediate Similarity	NPC105127
0.7802	Intermediate Similarity	NPC233936
0.7802	Intermediate Similarity	NPC71037
0.7799	Intermediate Similarity	NPC15801
0.7796	Intermediate Similarity	NPC95783
0.779	Intermediate Similarity	NPC55772
0.779	Intermediate Similarity	NPC283219
0.7789	Intermediate Similarity	NPC469928
0.7789	Intermediate Similarity	NPC142901
0.7784	Intermediate Similarity	NPC278434
0.7772	Intermediate Similarity	NPC475774
0.7772	Intermediate Similarity	NPC15102
0.7771	Intermediate Similarity	NPC469779
0.7771	Intermediate Similarity	NPC469784
0.7771	Intermediate Similarity	NPC469780
0.7771	Intermediate Similarity	NPC469783
0.7771	Intermediate Similarity	NPC469761
0.7771	Intermediate Similarity	NPC469767
0.7771	Intermediate Similarity	NPC469768
0.776	Intermediate Similarity	NPC163055
0.7751	Intermediate Similarity	NPC477549
0.7751	Intermediate Similarity	NPC295228
0.7747	Intermediate Similarity	NPC300688
0.7745	Intermediate Similarity	NPC125597
0.7744	Intermediate Similarity	NPC193777
0.774	Intermediate Similarity	NPC49217
0.7739	Intermediate Similarity	NPC470549
0.7734	Intermediate Similarity	NPC16352
0.773	Intermediate Similarity	NPC235684
0.7725	Intermediate Similarity	NPC469766
0.7725	Intermediate Similarity	NPC131017
0.7717	Intermediate Similarity	NPC284678
0.7716	Intermediate Similarity	NPC167860
0.7716	Intermediate Similarity	NPC123976

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 NPC204717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	679
0.2-0.3	794
0.3-0.4	1398
0.4-0.5	2637
0.5-0.6	2194
0.6-0.7	942
0.7-0.8	167
0.8-0.85	10
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD5575	Clinical (unspecified phase)
0.9195	High Similarity	NPD1038	Approved
0.9101	High Similarity	NPD484	Approved
0.8977	High Similarity	NPD1304	Clinical (unspecified phase)
0.8722	High Similarity	NPD7948	Phase 1
0.8556	High Similarity	NPD802	Phase 2
0.8438	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5612	Discontinued
0.8371	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.836	Intermediate Similarity	NPD2189	Approved
0.836	Intermediate Similarity	NPD2187	Approved
0.8333	Intermediate Similarity	NPD5065	Approved
0.8238	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD1325	Approved
0.8161	Intermediate Similarity	NPD1326	Approved
0.8161	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD3825	Phase 3
0.8042	Intermediate Similarity	NPD4511	Phase 1
0.798	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1392	Approved
0.7921	Intermediate Similarity	NPD9690	Approved
0.7921	Intermediate Similarity	NPD482	Approved
0.7919	Intermediate Similarity	NPD112	Approved
0.7919	Intermediate Similarity	NPD9705	Discontinued
0.7917	Intermediate Similarity	NPD4795	Phase 2
0.7914	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD6242	Discontinued
0.7895	Intermediate Similarity	NPD1739	Approved
0.7895	Intermediate Similarity	NPD1740	Approved
0.7853	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6595	Phase 3
0.7831	Intermediate Similarity	NPD1592	Phase 3
0.7818	Intermediate Similarity	NPD786	Approved
0.7789	Intermediate Similarity	NPD7112	Discontinued
0.7784	Intermediate Similarity	NPD926	Approved
0.7784	Intermediate Similarity	NPD925	Approved
0.7766	Intermediate Similarity	NPD9695	Approved
0.776	Intermediate Similarity	NPD2092	Phase 2
0.776	Intermediate Similarity	NPD2094	Phase 2
0.776	Intermediate Similarity	NPD2095	Phase 2
0.7759	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD3814	Phase 1
0.774	Intermediate Similarity	NPD424	Approved
0.774	Intermediate Similarity	NPD425	Approved
0.772	Intermediate Similarity	NPD3931	Approved
0.772	Intermediate Similarity	NPD3928	Approved
0.7717	Intermediate Similarity	NPD2096	Phase 2
0.7717	Intermediate Similarity	NPD2091	Phase 2
0.7707	Intermediate Similarity	NPD7603	Discontinued
0.7677	Intermediate Similarity	NPD5067	Phase 2
0.7677	Intermediate Similarity	NPD5066	Phase 2
0.7676	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4845	Discontinued
0.7667	Intermediate Similarity	NPD750	Phase 2
0.7656	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD2177	Approved
0.7656	Intermediate Similarity	NPD2175	Phase 3
0.7656	Intermediate Similarity	NPD2176	Approved
0.7641	Intermediate Similarity	NPD31	Approved
0.7641	Intermediate Similarity	NPD32	Approved
0.7641	Intermediate Similarity	NPD4034	Approved
0.7641	Intermediate Similarity	NPD4036	Approved
0.7641	Intermediate Similarity	NPD4035	Approved
0.7641	Intermediate Similarity	NPD4122	Approved
0.7641	Intermediate Similarity	NPD4037	Approved
0.7641	Intermediate Similarity	NPD4039	Approved
0.7641	Intermediate Similarity	NPD4038	Approved
0.7641	Intermediate Similarity	NPD4033	Approved
0.7638	Intermediate Similarity	NPD3330	Phase 1
0.7627	Intermediate Similarity	NPD5138	Approved
0.7627	Intermediate Similarity	NPD5140	Approved
0.7619	Intermediate Similarity	NPD1722	Approved
0.7619	Intermediate Similarity	NPD3404	Approved
0.7614	Intermediate Similarity	NPD5658	Approved
0.7598	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD8431	Approved
0.7588	Intermediate Similarity	NPD949	Phase 1
0.7568	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1768	Approved
0.7565	Intermediate Similarity	NPD8395	Approved
0.7565	Intermediate Similarity	NPD8396	Approved
0.7563	Intermediate Similarity	NPD7453	Approved
0.7563	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7222	Phase 2
0.7563	Intermediate Similarity	NPD7452	Approved
0.7553	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5901	Discontinued
0.7548	Intermediate Similarity	NPD5559	Phase 2
0.7541	Intermediate Similarity	NPD2144	Approved
0.7541	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6975	Discontinued
0.7514	Intermediate Similarity	NPD4462	Approved
0.7514	Intermediate Similarity	NPD4463	Approved
0.7513	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD3003	Approved
0.75	Intermediate Similarity	NPD2383	Phase 1
0.7488	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5255	Approved
0.7457	Intermediate Similarity	NPD3100	Discontinued
0.7451	Intermediate Similarity	NPD3354	Phase 2
0.7448	Intermediate Similarity	NPD4418	Discontinued
0.7446	Intermediate Similarity	NPD6159	Phase 2
0.7426	Intermediate Similarity	NPD2616	Phase 3
0.7426	Intermediate Similarity	NPD2615	Phase 3
0.7424	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3038	Discontinued
0.7416	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2172	Phase 1
0.7406	Intermediate Similarity	NPD7558	Phase 2
0.7405	Intermediate Similarity	NPD4076	Approved
0.7405	Intermediate Similarity	NPD4079	Approved
0.7403	Intermediate Similarity	NPD2781	Approved
0.74	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4703	Approved
0.7399	Intermediate Similarity	NPD4702	Approved
0.7391	Intermediate Similarity	NPD5100	Phase 3
0.7389	Intermediate Similarity	NPD2780	Approved
0.7389	Intermediate Similarity	NPD2782	Approved
0.7387	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1685	Approved
0.7374	Intermediate Similarity	NPD1684	Approved
0.7371	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6158	Phase 2
0.7371	Intermediate Similarity	NPD2952	Discontinued
0.7366	Intermediate Similarity	NPD2021	Discontinued
0.7356	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD706	Phase 1
0.7351	Intermediate Similarity	NPD3506	Approved
0.7351	Intermediate Similarity	NPD3505	Approved
0.7344	Intermediate Similarity	NPD996	Phase 2
0.7344	Intermediate Similarity	NPD994	Phase 2
0.7344	Intermediate Similarity	NPD9689	Approved
0.7327	Intermediate Similarity	NPD5936	Approved
0.7327	Intermediate Similarity	NPD7470	Discontinued
0.7327	Intermediate Similarity	NPD5939	Approved
0.7322	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2844	Phase 3
0.7308	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2381	Approved
0.7297	Intermediate Similarity	NPD2380	Approved
0.7297	Intermediate Similarity	NPD2382	Approved
0.7296	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2916	Discontinued
0.7263	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3921	Approved
0.7254	Intermediate Similarity	NPD3924	Approved
0.7254	Intermediate Similarity	NPD3923	Approved
0.7254	Intermediate Similarity	NPD3922	Approved
0.724	Intermediate Similarity	NPD5117	Phase 2
0.7234	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4204	Approved
0.7234	Intermediate Similarity	NPD4203	Approved
0.7225	Intermediate Similarity	NPD3813	Approved
0.7225	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1403	Approved
0.7222	Intermediate Similarity	NPD1404	Approved
0.722	Intermediate Similarity	NPD5903	Approved
0.722	Intermediate Similarity	NPD5902	Approved
0.7214	Intermediate Similarity	NPD6290	Phase 2
0.7206	Intermediate Similarity	NPD8093	Discontinued
0.7204	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5913	Phase 3
0.72	Intermediate Similarity	NPD5426	Phase 3
0.7196	Intermediate Similarity	NPD5596	Phase 2
0.7194	Intermediate Similarity	NPD1218	Approved
0.7194	Intermediate Similarity	NPD1219	Approved
0.7192	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3013	Phase 3
0.7186	Intermediate Similarity	NPD8073	Approved
0.7182	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3017	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4454	Phase 2
0.7175	Intermediate Similarity	NPD2882	Phase 1
0.7171	Intermediate Similarity	NPD8094	Discontinued
0.7163	Intermediate Similarity	NPD6494	Phase 2
0.7163	Intermediate Similarity	NPD3402	Phase 1
0.7157	Intermediate Similarity	NPD4502	Phase 2
0.7151	Intermediate Similarity	NPD4128	Approved
0.7151	Intermediate Similarity	NPD2789	Approved
0.715	Intermediate Similarity	NPD4886	Phase 2
0.715	Intermediate Similarity	NPD1213	Phase 3
0.7143	Intermediate Similarity	NPD3178	Discontinued
0.7135	Intermediate Similarity	NPD2837	Discontinued
0.7135	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4551	Phase 2
0.7127	Intermediate Similarity	NPD5599	Discontinued
0.7121	Intermediate Similarity	NPD9687	Approved
0.7121	Intermediate Similarity	NPD9688	Approved
0.712	Intermediate Similarity	NPD2762	Phase 2
0.7111	Intermediate Similarity	NPD9383	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