NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.1
Volume:	242.917
LogP:	-0.906
LogD:	0.584
LogS:	-2.598
# Rotatable Bonds:	1
TPSA:	85.35
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	3.403
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.708
MDCK Permeability:	5.455200152937323e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	39.16563415527344%
Volume Distribution (VD):	0.879
Pgp-substrate:	65.45578002929688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.397
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.484
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.007
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.736
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.364
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.382
Carcinogencity:	0.474
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC476098

Natural Product ID:	NPC476098
*Common Name:**	Hyrtioerectine B
IUPAC Name:	(1R,3R)-6-hydroxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	WYQWRMWMBQUYSD-KSBSHMNSSA-N
Standard InCHI:	InChI=1S/C13H14N2O3/c1-6-12-9(5-11(14-6)13(17)18)8-4-7(16)2-3-10(8)15-12/h2-4,6,11,14-16H,5H2,1H3,(H,17,18)/t6-,11-/m1/s1
SMILES:	CC1C2=C(CC(N1)C(=O)O)C3=C(N2)C=CC(=C3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526126
PubChem CID:	11665960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[20000782]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22695182]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11919	Hyrtios reticulatus	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[525660]

☑ 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 NPC476098 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	328
0.1-0.2	2716
0.2-0.3	13563
0.3-0.4	10305
0.4-0.5	9710
0.5-0.6	3338
0.6-0.7	2000
0.7-0.8	685
0.8-0.85	40
0.85-0.9	6
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9105	High Similarity	NPC270918
0.9091	High Similarity	NPC315491
0.9091	High Similarity	NPC45459
0.8925	High Similarity	NPC276517
0.8889	High Similarity	NPC213308
0.8883	High Similarity	NPC306376
0.8833	High Similarity	NPC219336
0.8778	High Similarity	NPC217372
0.8778	High Similarity	NPC183662
0.8778	High Similarity	NPC15573
0.8643	High Similarity	NPC469928
0.8534	High Similarity	NPC156704
0.852	High Similarity	NPC88008
0.8478	Intermediate Similarity	NPC469896
0.8426	Intermediate Similarity	NPC321428
0.8402	Intermediate Similarity	NPC249040
0.8396	Intermediate Similarity	NPC314002
0.8364	Intermediate Similarity	NPC171393
0.8364	Intermediate Similarity	NPC295452
0.8342	Intermediate Similarity	NPC204717
0.8342	Intermediate Similarity	NPC141454
0.8333	Intermediate Similarity	NPC53344
0.8289	Intermediate Similarity	NPC220765
0.8254	Intermediate Similarity	NPC171171
0.8226	Intermediate Similarity	NPC88363
0.8186	Intermediate Similarity	NPC330009
0.8182	Intermediate Similarity	NPC165599
0.8178	Intermediate Similarity	NPC15801
0.8159	Intermediate Similarity	NPC325297
0.8141	Intermediate Similarity	NPC475070
0.8135	Intermediate Similarity	NPC99666
0.8128	Intermediate Similarity	NPC126709
0.8128	Intermediate Similarity	NPC248041
0.8116	Intermediate Similarity	NPC472099
0.8107	Intermediate Similarity	NPC96321
0.8095	Intermediate Similarity	NPC319232
0.8095	Intermediate Similarity	NPC24370
0.8079	Intermediate Similarity	NPC294375
0.8077	Intermediate Similarity	NPC60621
0.8075	Intermediate Similarity	NPC184964
0.8069	Intermediate Similarity	NPC476116
0.806	Intermediate Similarity	NPC244741
0.8049	Intermediate Similarity	NPC118228
0.8032	Intermediate Similarity	NPC283219
0.8032	Intermediate Similarity	NPC72980
0.803	Intermediate Similarity	NPC5145
0.803	Intermediate Similarity	NPC471304
0.8021	Intermediate Similarity	NPC267885
0.8019	Intermediate Similarity	NPC303658
0.801	Intermediate Similarity	NPC300156
0.801	Intermediate Similarity	NPC148183
0.801	Intermediate Similarity	NPC152768
0.8009	Intermediate Similarity	NPC184225
0.8009	Intermediate Similarity	NPC214142
0.7991	Intermediate Similarity	NPC207686
0.799	Intermediate Similarity	NPC9894
0.7981	Intermediate Similarity	NPC74360
0.798	Intermediate Similarity	NPC476167
0.7972	Intermediate Similarity	NPC304307
0.7972	Intermediate Similarity	NPC34580
0.7972	Intermediate Similarity	NPC118559
0.7972	Intermediate Similarity	NPC124920
0.7972	Intermediate Similarity	NPC261251
0.797	Intermediate Similarity	NPC77555
0.7968	Intermediate Similarity	NPC149155
0.7968	Intermediate Similarity	NPC203468
0.7968	Intermediate Similarity	NPC110500
0.7951	Intermediate Similarity	NPC472098
0.7951	Intermediate Similarity	NPC219087
0.7943	Intermediate Similarity	NPC276657
0.7941	Intermediate Similarity	NPC309845
0.7934	Intermediate Similarity	NPC100547
0.7931	Intermediate Similarity	NPC39679
0.7931	Intermediate Similarity	NPC171787
0.7929	Intermediate Similarity	NPC192315
0.7927	Intermediate Similarity	NPC46580
0.7923	Intermediate Similarity	NPC322064
0.7923	Intermediate Similarity	NPC74969
0.7913	Intermediate Similarity	NPC89508
0.791	Intermediate Similarity	NPC223427
0.7907	Intermediate Similarity	NPC475720
0.7907	Intermediate Similarity	NPC474192
0.7906	Intermediate Similarity	NPC176127
0.7897	Intermediate Similarity	NPC95240
0.7897	Intermediate Similarity	NPC322135
0.7897	Intermediate Similarity	NPC223409
0.789	Intermediate Similarity	NPC82472
0.7887	Intermediate Similarity	NPC128751
0.7887	Intermediate Similarity	NPC175474
0.7887	Intermediate Similarity	NPC246700
0.7885	Intermediate Similarity	NPC305984
0.7884	Intermediate Similarity	NPC111275
0.7884	Intermediate Similarity	NPC145885
0.7884	Intermediate Similarity	NPC84827
0.7884	Intermediate Similarity	NPC14113
0.7882	Intermediate Similarity	NPC283117
0.7876	Intermediate Similarity	NPC62749
0.787	Intermediate Similarity	NPC323752
0.786	Intermediate Similarity	NPC14288
0.785	Intermediate Similarity	NPC311906
0.7847	Intermediate Similarity	NPC184408
0.7846	Intermediate Similarity	NPC469497
0.7846	Intermediate Similarity	NPC106833
0.7838	Intermediate Similarity	NPC178858
0.7834	Intermediate Similarity	NPC97902
0.7828	Intermediate Similarity	NPC251090
0.7824	Intermediate Similarity	NPC54803
0.7824	Intermediate Similarity	NPC321592
0.782	Intermediate Similarity	NPC473317
0.7819	Intermediate Similarity	NPC474409
0.7817	Intermediate Similarity	NPC307963
0.7808	Intermediate Similarity	NPC470784
0.7808	Intermediate Similarity	NPC41679
0.7807	Intermediate Similarity	NPC74619
0.7804	Intermediate Similarity	NPC478078
0.7799	Intermediate Similarity	NPC312645
0.7795	Intermediate Similarity	NPC102338
0.7795	Intermediate Similarity	NPC196251
0.7795	Intermediate Similarity	NPC63199
0.7795	Intermediate Similarity	NPC111602
0.7788	Intermediate Similarity	NPC323198
0.7788	Intermediate Similarity	NPC284888
0.7784	Intermediate Similarity	NPC235684
0.7783	Intermediate Similarity	NPC132539
0.7778	Intermediate Similarity	NPC473800
0.7773	Intermediate Similarity	NPC475816
0.7772	Intermediate Similarity	NPC57398
0.7767	Intermediate Similarity	NPC194740
0.7763	Intermediate Similarity	NPC184680
0.7762	Intermediate Similarity	NPC264285
0.7761	Intermediate Similarity	NPC313985
0.7761	Intermediate Similarity	NPC49196
0.7761	Intermediate Similarity	NPC195461
0.7761	Intermediate Similarity	NPC79129
0.7761	Intermediate Similarity	NPC249150
0.7761	Intermediate Similarity	NPC176538
0.7761	Intermediate Similarity	NPC81654
0.7754	Intermediate Similarity	NPC78020
0.7752	Intermediate Similarity	NPC245055
0.7752	Intermediate Similarity	NPC33064
0.7752	Intermediate Similarity	NPC182222
0.775	Intermediate Similarity	NPC50503
0.7746	Intermediate Similarity	NPC229893
0.7746	Intermediate Similarity	NPC51388
0.7745	Intermediate Similarity	NPC45190
0.7734	Intermediate Similarity	NPC134848
0.7731	Intermediate Similarity	NPC326363
0.7729	Intermediate Similarity	NPC87413
0.7729	Intermediate Similarity	NPC82370
0.7727	Intermediate Similarity	NPC45850
0.7727	Intermediate Similarity	NPC470785
0.7717	Intermediate Similarity	NPC477549
0.7714	Intermediate Similarity	NPC476041
0.7714	Intermediate Similarity	NPC304926
0.7711	Intermediate Similarity	NPC280714
0.771	Intermediate Similarity	NPC21638
0.771	Intermediate Similarity	NPC125597
0.7708	Intermediate Similarity	NPC91179
0.7705	Intermediate Similarity	NPC141353
0.7704	Intermediate Similarity	NPC296527
0.7704	Intermediate Similarity	NPC32771
0.77	Intermediate Similarity	NPC153042
0.77	Intermediate Similarity	NPC280272
0.7692	Intermediate Similarity	NPC118940
0.7692	Intermediate Similarity	NPC315555
0.7688	Intermediate Similarity	NPC326634
0.7685	Intermediate Similarity	NPC211813
0.7684	Intermediate Similarity	NPC303225
0.7681	Intermediate Similarity	NPC234999
0.7678	Intermediate Similarity	NPC473041
0.7677	Intermediate Similarity	NPC324149
0.7673	Intermediate Similarity	NPC329793
0.7668	Intermediate Similarity	NPC314394
0.7667	Intermediate Similarity	NPC3207
0.7665	Intermediate Similarity	NPC83111
0.7665	Intermediate Similarity	NPC76748
0.7662	Intermediate Similarity	NPC52557
0.7659	Intermediate Similarity	NPC475841
0.7659	Intermediate Similarity	NPC474145
0.7656	Intermediate Similarity	NPC469592
0.7656	Intermediate Similarity	NPC471080
0.7656	Intermediate Similarity	NPC55772
0.7656	Intermediate Similarity	NPC39500
0.7642	Intermediate Similarity	NPC255110
0.7638	Intermediate Similarity	NPC230403
0.7635	Intermediate Similarity	NPC471944
0.763	Intermediate Similarity	NPC293151
0.763	Intermediate Similarity	NPC27041
0.7629	Intermediate Similarity	NPC212535
0.7626	Intermediate Similarity	NPC92111
0.7615	Intermediate Similarity	NPC474701
0.7615	Intermediate Similarity	NPC260434
0.7614	Intermediate Similarity	NPC221873
0.7614	Intermediate Similarity	NPC321708
0.7612	Intermediate Similarity	NPC90229
0.7608	Intermediate Similarity	NPC475778
0.76	Intermediate Similarity	NPC289299
0.76	Intermediate Similarity	NPC57994
0.7591	Intermediate Similarity	NPC325976
0.7586	Intermediate Similarity	NPC214428

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 NPC476098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	555
0.2-0.3	900
0.3-0.4	1144
0.4-0.5	2563
0.5-0.6	2691
0.6-0.7	957
0.7-0.8	137
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD484	Approved
0.8019	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8009	Intermediate Similarity	NPD7603	Discontinued
0.8	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD482	Approved
0.7946	Intermediate Similarity	NPD2844	Phase 3
0.7931	Intermediate Similarity	NPD2916	Discontinued
0.7926	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6376	Discontinued
0.7826	Intermediate Similarity	NPD3243	Approved
0.7824	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1038	Approved
0.7812	Intermediate Similarity	NPD2094	Phase 2
0.7812	Intermediate Similarity	NPD2095	Phase 2
0.7812	Intermediate Similarity	NPD2092	Phase 2
0.7793	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD2096	Phase 2
0.7772	Intermediate Similarity	NPD2091	Phase 2
0.7761	Intermediate Similarity	NPD4600	Approved
0.7761	Intermediate Similarity	NPD4601	Approved
0.7742	Intermediate Similarity	NPD4885	Approved
0.7725	Intermediate Similarity	NPD750	Phase 2
0.772	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD1326	Approved
0.7713	Intermediate Similarity	NPD1325	Approved
0.7711	Intermediate Similarity	NPD2176	Approved
0.7711	Intermediate Similarity	NPD2177	Approved
0.7711	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2175	Phase 3
0.77	Intermediate Similarity	NPD7948	Phase 1
0.77	Intermediate Similarity	NPD5003	Discontinued
0.7638	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5901	Discontinued
0.76	Intermediate Similarity	NPD4602	Approved
0.76	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD5658	Approved
0.7576	Intermediate Similarity	NPD2564	Approved
0.7576	Intermediate Similarity	NPD2565	Phase 2
0.7573	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2383	Phase 1
0.756	Intermediate Similarity	NPD7470	Discontinued
0.7536	Intermediate Similarity	NPD4897	Phase 2
0.7535	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4500	Approved
0.75	Intermediate Similarity	NPD4501	Approved
0.75	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5612	Discontinued
0.7487	Intermediate Similarity	NPD4499	Approved
0.7477	Intermediate Similarity	NPD4845	Discontinued
0.7475	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7222	Phase 2
0.7452	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6242	Discontinued
0.743	Intermediate Similarity	NPD5632	Approved
0.7426	Intermediate Similarity	NPD4418	Discontinued
0.7423	Intermediate Similarity	NPD6159	Phase 2
0.7404	Intermediate Similarity	NPD3003	Approved
0.7393	Intermediate Similarity	NPD5939	Approved
0.7393	Intermediate Similarity	NPD5936	Approved
0.7379	Intermediate Similarity	NPD4511	Phase 1
0.7376	Intermediate Similarity	NPD802	Phase 2
0.7373	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD1768	Approved
0.7356	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3354	Phase 2
0.7348	Intermediate Similarity	NPD5482	Discontinued
0.733	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8463	Approved
0.7327	Intermediate Similarity	NPD6665	Discontinued
0.7327	Intermediate Similarity	NPD5507	Approved
0.7327	Intermediate Similarity	NPD5506	Approved
0.732	Intermediate Similarity	NPD5065	Approved
0.731	Intermediate Similarity	NPD3178	Discontinued
0.7286	Intermediate Similarity	NPD7453	Approved
0.7286	Intermediate Similarity	NPD7452	Approved
0.7282	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3814	Phase 1
0.7264	Intermediate Similarity	NPD1534	Approved
0.7261	Intermediate Similarity	NPD8358	Approved
0.7259	Intermediate Similarity	NPD6452	Discontinued
0.7246	Intermediate Similarity	NPD1740	Approved
0.7246	Intermediate Similarity	NPD1739	Approved
0.724	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3258	Approved
0.7233	Intermediate Similarity	NPD4397	Phase 1
0.723	Intermediate Similarity	NPD4502	Phase 2
0.723	Intermediate Similarity	NPD5416	Discontinued
0.7229	Intermediate Similarity	NPD4558	Phase 2
0.7225	Intermediate Similarity	NPD2920	Discontinued
0.7225	Intermediate Similarity	NPD5138	Approved
0.7225	Intermediate Similarity	NPD5140	Approved
0.7225	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4203	Approved
0.7222	Intermediate Similarity	NPD4204	Approved
0.7222	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5512	Phase 3
0.7214	Intermediate Similarity	NPD4948	Discontinued
0.7207	Intermediate Similarity	NPD5559	Phase 2
0.7204	Intermediate Similarity	NPD6290	Phase 2
0.72	Intermediate Similarity	NPD2951	Discontinued
0.7198	Intermediate Similarity	NPD8396	Approved
0.7198	Intermediate Similarity	NPD8395	Approved
0.7194	Intermediate Similarity	NPD2381	Approved
0.7194	Intermediate Similarity	NPD2380	Approved
0.7194	Intermediate Similarity	NPD2382	Approved
0.7192	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4795	Phase 2
0.719	Intermediate Similarity	NPD5426	Phase 3
0.7188	Intermediate Similarity	NPD3746	Discontinued
0.7186	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7112	Discontinued
0.717	Intermediate Similarity	NPD2509	Approved
0.717	Intermediate Similarity	NPD2510	Approved
0.715	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4520	Approved
0.7136	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3257	Approved
0.713	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1392	Approved
0.7117	Intermediate Similarity	NPD3263	Phase 3
0.7116	Intermediate Similarity	NPD8093	Discontinued
0.7116	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2762	Phase 2
0.7109	Intermediate Similarity	NPD8098	Approved
0.7108	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1592	Phase 3
0.7103	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5596	Phase 2
0.7098	Intermediate Similarity	NPD5479	Discontinued
0.7097	Intermediate Similarity	NPD3389	Approved
0.7097	Intermediate Similarity	NPD3394	Approved
0.7097	Intermediate Similarity	NPD3393	Approved
0.7094	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3006	Discontinued
0.709	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2189	Approved
0.7089	Intermediate Similarity	NPD2187	Approved
0.7085	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1684	Approved
0.7083	Intermediate Similarity	NPD1685	Approved
0.7083	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7194	Discontinued
0.7077	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6158	Phase 2
0.7074	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8356	Approved
0.7059	Intermediate Similarity	NPD7955	Approved
0.7059	Intermediate Similarity	NPD7956	Approved
0.7056	Intermediate Similarity	NPD9690	Approved
0.7053	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5902	Approved
0.7051	Intermediate Similarity	NPD5903	Approved
0.7051	Intermediate Similarity	NPD3986	Discontinued
0.7042	Intermediate Similarity	NPD5429	Discontinued
0.7039	Intermediate Similarity	NPD9695	Approved
0.7037	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8097	Phase 3
0.7037	Intermediate Similarity	NPD8096	Phase 3
0.7035	Intermediate Similarity	NPD7797	Approved
0.7035	Intermediate Similarity	NPD7796	Approved
0.7035	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD9705	Discontinued
0.7031	Intermediate Similarity	NPD112	Approved
0.7029	Intermediate Similarity	NPD7708	Approved
0.7028	Intermediate Similarity	NPD31	Approved
0.7028	Intermediate Similarity	NPD4033	Approved
0.7028	Intermediate Similarity	NPD4039	Approved
0.7028	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD4037	Approved
0.7028	Intermediate Similarity	NPD32	Approved
0.7028	Intermediate Similarity	NPD4035	Approved
0.7028	Intermediate Similarity	NPD4122	Approved
0.7028	Intermediate Similarity	NPD4036	Approved
0.7028	Intermediate Similarity	NPD4034	Approved
0.7028	Intermediate Similarity	NPD4038	Approved
0.7024	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5913	Phase 3
0.7023	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4463	Approved
0.7021	Intermediate Similarity	NPD4462	Approved
0.7009	Intermediate Similarity	NPD8430	Approved
0.7009	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7618	Phase 3
0.7005	Intermediate Similarity	NPD7619	Phase 3
0.7	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5445	Approved
0.7	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5488	Discontinued
0.6995	Remote Similarity	NPD5256	Discontinued
0.6995	Remote Similarity	NPD5530	Phase 1
0.6991	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7946	Pre-registration

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