NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	202.07
Volume:	199.535
LogP:	1.647
LogD:	1.604
LogS:	-2.975
# Rotatable Bonds:	0
TPSA:	65.12
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	2.531
Fsp3:	0.182
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:	-5.108
MDCK Permeability:	5.20493631483987e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.831
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	54.53784942626953%
Volume Distribution (VD):	1.28
Pgp-substrate:	32.049922943115234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.779
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	10.776
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.473
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.466
Rat Oral Acute Toxicity:	0.643
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.638
Carcinogencity:	0.054
Eye Corrosion:	0.004
Eye Irritation:	0.233
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC270918

Natural Product ID:	NPC270918
*Common Name:**	6-Hydroxy-3,4-Dihydro-1-Oxo-Beta-Carboline
IUPAC Name:	6-hydroxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
Synonyms:
Standard InCHIKey:	WNGPRJOWLUNBCE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10N2O2/c14-6-1-2-9-8(5-6)7-3-4-12-11(15)10(7)13-9/h1-2,5,13-14H,3-4H2,(H,12,15)
SMILES:	Oc1ccc2c(c1)c1CCNC(=O)c1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL397215
PubChem CID:	6452337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]

☑ 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	4
MIC	1

Activity Type	# Activity
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3080	Individual Protein	Metabotropic glutamate receptor 1	Rattus norvegicus	IC50	>	10000.0	nM	PMID[527954]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	989100.0	nM	PMID[527955]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	100.0	ug.mL-1	PMID[527956]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	100.0	ug.mL-1	PMID[527956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	989100.0	nM	PMID[527955]

☑ 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 NPC270918 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	512
0.1-0.2	3963
0.2-0.3	12974
0.3-0.4	9407
0.4-0.5	10457
0.5-0.6	2806
0.6-0.7	2045
0.7-0.8	495
0.8-0.85	33
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9105	High Similarity	NPC476098
0.8607	High Similarity	NPC322064
0.8586	High Similarity	NPC276517
0.8557	High Similarity	NPC213308
0.8462	Intermediate Similarity	NPC45459
0.8462	Intermediate Similarity	NPC315491
0.8389	Intermediate Similarity	NPC207686
0.83	Intermediate Similarity	NPC321428
0.8276	Intermediate Similarity	NPC219087
0.8271	Intermediate Similarity	NPC477549
0.8261	Intermediate Similarity	NPC276657
0.8259	Intermediate Similarity	NPC171787
0.8227	Intermediate Similarity	NPC9894
0.8227	Intermediate Similarity	NPC294375
0.8214	Intermediate Similarity	NPC141454
0.8209	Intermediate Similarity	NPC53344
0.8173	Intermediate Similarity	NPC306376
0.8168	Intermediate Similarity	NPC314002
0.816	Intermediate Similarity	NPC194740
0.8158	Intermediate Similarity	NPC220765
0.8155	Intermediate Similarity	NPC469928
0.8141	Intermediate Similarity	NPC471944
0.814	Intermediate Similarity	NPC97902
0.8128	Intermediate Similarity	NPC325297
0.8122	Intermediate Similarity	NPC156704
0.8119	Intermediate Similarity	NPC88008
0.8115	Intermediate Similarity	NPC204717
0.8113	Intermediate Similarity	NPC157931
0.8095	Intermediate Similarity	NPC220851
0.809	Intermediate Similarity	NPC249040
0.8077	Intermediate Similarity	NPC264285
0.8065	Intermediate Similarity	NPC15801
0.806	Intermediate Similarity	NPC165599
0.8042	Intermediate Similarity	NPC217372
0.8042	Intermediate Similarity	NPC15573
0.8042	Intermediate Similarity	NPC183662
0.8031	Intermediate Similarity	NPC171171
0.803	Intermediate Similarity	NPC283117
0.803	Intermediate Similarity	NPC244741
0.8029	Intermediate Similarity	NPC27041
0.801	Intermediate Similarity	NPC99666
0.801	Intermediate Similarity	NPC211813
0.8	Intermediate Similarity	NPC219336
0.8	Intermediate Similarity	NPC309845
0.8	Intermediate Similarity	NPC323969
0.8	Intermediate Similarity	NPC88363
0.798	Intermediate Similarity	NPC300156
0.798	Intermediate Similarity	NPC45190
0.797	Intermediate Similarity	NPC134848
0.7952	Intermediate Similarity	NPC74360
0.7949	Intermediate Similarity	NPC221873
0.7947	Intermediate Similarity	NPC184964
0.7944	Intermediate Similarity	NPC478078
0.7943	Intermediate Similarity	NPC305984
0.7905	Intermediate Similarity	NPC303658
0.7902	Intermediate Similarity	NPC210828
0.7902	Intermediate Similarity	NPC39679
0.7902	Intermediate Similarity	NPC86834
0.79	Intermediate Similarity	NPC184225
0.7892	Intermediate Similarity	NPC178858
0.7854	Intermediate Similarity	NPC183777
0.785	Intermediate Similarity	NPC77555
0.7847	Intermediate Similarity	NPC118228
0.7843	Intermediate Similarity	NPC475070
0.784	Intermediate Similarity	NPC16352
0.7812	Intermediate Similarity	NPC72980
0.7806	Intermediate Similarity	NPC46580
0.7799	Intermediate Similarity	NPC89508
0.7788	Intermediate Similarity	NPC23294
0.7783	Intermediate Similarity	NPC288987
0.7783	Intermediate Similarity	NPC74619
0.7778	Intermediate Similarity	NPC476116
0.7758	Intermediate Similarity	NPC295452
0.7758	Intermediate Similarity	NPC171393
0.7749	Intermediate Similarity	NPC303225
0.7746	Intermediate Similarity	NPC472099
0.7742	Intermediate Similarity	NPC311906
0.774	Intermediate Similarity	NPC471304
0.774	Intermediate Similarity	NPC303951
0.774	Intermediate Similarity	NPC5145
0.7731	Intermediate Similarity	NPC319232
0.7731	Intermediate Similarity	NPC24370
0.7727	Intermediate Similarity	NPC83111
0.7725	Intermediate Similarity	NPC330009
0.7723	Intermediate Similarity	NPC131887
0.7721	Intermediate Similarity	NPC229893
0.7721	Intermediate Similarity	NPC122436
0.7707	Intermediate Similarity	NPC223427
0.7704	Intermediate Similarity	NPC133003
0.7703	Intermediate Similarity	NPC87413
0.7703	Intermediate Similarity	NPC82370
0.7703	Intermediate Similarity	NPC470784
0.7696	Intermediate Similarity	NPC474409
0.7692	Intermediate Similarity	NPC176127
0.7689	Intermediate Similarity	NPC312645
0.7689	Intermediate Similarity	NPC293151
0.7685	Intermediate Similarity	NPC280714
0.768	Intermediate Similarity	NPC469896
0.7678	Intermediate Similarity	NPC477979
0.7677	Intermediate Similarity	NPC128751
0.7677	Intermediate Similarity	NPC246700
0.7675	Intermediate Similarity	NPC473800
0.7674	Intermediate Similarity	NPC478141
0.7673	Intermediate Similarity	NPC74153
0.7673	Intermediate Similarity	NPC90229
0.767	Intermediate Similarity	NPC132539
0.7668	Intermediate Similarity	NPC475816
0.7661	Intermediate Similarity	NPC471762
0.7659	Intermediate Similarity	NPC57398
0.7658	Intermediate Similarity	NPC184680
0.7653	Intermediate Similarity	NPC184408
0.7653	Intermediate Similarity	NPC96321
0.765	Intermediate Similarity	NPC214142
0.7647	Intermediate Similarity	NPC182222
0.7642	Intermediate Similarity	NPC3207
0.7638	Intermediate Similarity	NPC324091
0.7638	Intermediate Similarity	NPC106833
0.7638	Intermediate Similarity	NPC469497
0.7636	Intermediate Similarity	NPC132329
0.7635	Intermediate Similarity	NPC192315
0.7633	Intermediate Similarity	NPC175602
0.7628	Intermediate Similarity	NPC60621
0.7626	Intermediate Similarity	NPC326363
0.7624	Intermediate Similarity	NPC251090
0.7623	Intermediate Similarity	NPC470785
0.7615	Intermediate Similarity	NPC304307
0.7615	Intermediate Similarity	NPC118559
0.7615	Intermediate Similarity	NPC257851
0.7615	Intermediate Similarity	NPC261251
0.7615	Intermediate Similarity	NPC34580
0.7615	Intermediate Similarity	NPC124920
0.7614	Intermediate Similarity	NPC241025
0.7612	Intermediate Similarity	NPC307963
0.7612	Intermediate Similarity	NPC473821
0.7611	Intermediate Similarity	NPC160898
0.7606	Intermediate Similarity	NPC469727
0.7598	Intermediate Similarity	NPC476167
0.759	Intermediate Similarity	NPC91179
0.7583	Intermediate Similarity	NPC12344
0.7583	Intermediate Similarity	NPC110182
0.7583	Intermediate Similarity	NPC118940
0.758	Intermediate Similarity	NPC100547
0.7577	Intermediate Similarity	NPC111275
0.7574	Intermediate Similarity	NPC326634
0.757	Intermediate Similarity	NPC247803
0.757	Intermediate Similarity	NPC46561
0.7562	Intermediate Similarity	NPC324149
0.7561	Intermediate Similarity	NPC176538
0.7559	Intermediate Similarity	NPC148183
0.7559	Intermediate Similarity	NPC152768
0.7558	Intermediate Similarity	NPC51388
0.7557	Intermediate Similarity	NPC200553
0.7557	Intermediate Similarity	NPC279189
0.755	Intermediate Similarity	NPC144381
0.7547	Intermediate Similarity	NPC316181
0.7547	Intermediate Similarity	NPC74562
0.7547	Intermediate Similarity	NPC151781
0.7545	Intermediate Similarity	NPC322135
0.7545	Intermediate Similarity	NPC95240
0.7545	Intermediate Similarity	NPC82472
0.7545	Intermediate Similarity	NPC223409
0.7538	Intermediate Similarity	NPC278434
0.7536	Intermediate Similarity	NPC53144
0.7536	Intermediate Similarity	NPC200836
0.7535	Intermediate Similarity	NPC269270
0.7526	Intermediate Similarity	NPC151635
0.7525	Intermediate Similarity	NPC230403
0.7525	Intermediate Similarity	NPC269886
0.7525	Intermediate Similarity	NPC472210
0.7525	Intermediate Similarity	NPC472295
0.7525	Intermediate Similarity	NPC247735
0.7525	Intermediate Similarity	NPC81802
0.7524	Intermediate Similarity	NPC61038
0.7523	Intermediate Similarity	NPC323752
0.7523	Intermediate Similarity	NPC179287
0.7523	Intermediate Similarity	NPC284888
0.7523	Intermediate Similarity	NPC472285
0.7512	Intermediate Similarity	NPC4687
0.7512	Intermediate Similarity	NPC249583
0.7511	Intermediate Similarity	NPC63971
0.7511	Intermediate Similarity	NPC14288
0.7511	Intermediate Similarity	NPC260434
0.7511	Intermediate Similarity	NPC91868
0.75	Intermediate Similarity	NPC296527
0.75	Intermediate Similarity	NPC153042
0.75	Intermediate Similarity	NPC150239
0.75	Intermediate Similarity	NPC32771
0.75	Intermediate Similarity	NPC66777
0.75	Intermediate Similarity	NPC14686
0.75	Intermediate Similarity	NPC272174
0.7489	Intermediate Similarity	NPC325976
0.7488	Intermediate Similarity	NPC202812
0.7487	Intermediate Similarity	NPC194040
0.7487	Intermediate Similarity	NPC62749
0.7487	Intermediate Similarity	NPC160381
0.7477	Intermediate Similarity	NPC474192
0.7477	Intermediate Similarity	NPC475720
0.7477	Intermediate Similarity	NPC321592
0.7477	Intermediate Similarity	NPC54803
0.7467	Intermediate Similarity	NPC41679

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 NPC270918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	633
0.2-0.3	859
0.3-0.4	1328
0.4-0.5	2758
0.5-0.6	2306
0.6-0.7	891
0.7-0.8	100
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8535	High Similarity	NPD6376	Discontinued
0.8462	Intermediate Similarity	NPD484	Approved
0.8436	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD2916	Discontinued
0.7971	Intermediate Similarity	NPD3243	Approved
0.7944	Intermediate Similarity	NPD4845	Discontinued
0.7905	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7603	Discontinued
0.7879	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD4558	Phase 2
0.7717	Intermediate Similarity	NPD4885	Approved
0.7689	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5901	Discontinued
0.7664	Intermediate Similarity	NPD6242	Discontinued
0.7614	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1038	Approved
0.7596	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4897	Phase 2
0.7568	Intermediate Similarity	NPD2951	Discontinued
0.7512	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3746	Discontinued
0.7454	Intermediate Similarity	NPD3258	Approved
0.745	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2844	Phase 3
0.7438	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7948	Phase 1
0.7409	Intermediate Similarity	NPD1325	Approved
0.7409	Intermediate Similarity	NPD1326	Approved
0.7395	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD5658	Approved
0.7385	Intermediate Similarity	NPD5506	Approved
0.7385	Intermediate Similarity	NPD5507	Approved
0.7385	Intermediate Similarity	NPD482	Approved
0.7382	Intermediate Similarity	NPD8463	Approved
0.7371	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3257	Approved
0.7347	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5426	Phase 3
0.733	Intermediate Similarity	NPD3263	Phase 3
0.7315	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4948	Discontinued
0.7273	Intermediate Similarity	NPD6209	Approved
0.7269	Intermediate Similarity	NPD5293	Phase 2
0.7269	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5559	Phase 2
0.726	Intermediate Similarity	NPD2175	Phase 3
0.726	Intermediate Similarity	NPD2177	Approved
0.726	Intermediate Similarity	NPD2176	Approved
0.7253	Intermediate Similarity	NPD5482	Discontinued
0.725	Intermediate Similarity	NPD2092	Phase 2
0.725	Intermediate Similarity	NPD2095	Phase 2
0.725	Intermediate Similarity	NPD2094	Phase 2
0.7248	Intermediate Similarity	NPD5632	Approved
0.7236	Intermediate Similarity	NPD5445	Approved
0.7235	Intermediate Similarity	NPD5612	Discontinued
0.7232	Intermediate Similarity	NPD5479	Discontinued
0.7227	Intermediate Similarity	NPD6531	Approved
0.7227	Intermediate Similarity	NPD6530	Approved
0.7225	Intermediate Similarity	NPD4601	Approved
0.7225	Intermediate Similarity	NPD4600	Approved
0.7217	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2096	Phase 2
0.7214	Intermediate Similarity	NPD2091	Phase 2
0.7214	Intermediate Similarity	NPD1096	Discontinued
0.72	Intermediate Similarity	NPD3178	Discontinued
0.7198	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4511	Phase 1
0.7184	Intermediate Similarity	NPD802	Phase 2
0.7179	Intermediate Similarity	NPD3986	Discontinued
0.7177	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6999	Discontinued
0.7168	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD3962	Phase 2
0.7155	Intermediate Similarity	NPD3959	Phase 2
0.7143	Intermediate Similarity	NPD6164	Phase 2
0.7143	Intermediate Similarity	NPD4328	Approved
0.7143	Intermediate Similarity	NPD6165	Phase 2
0.713	Intermediate Similarity	NPD5416	Discontinued
0.713	Intermediate Similarity	NPD7470	Discontinued
0.7123	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5065	Approved
0.7118	Intermediate Similarity	NPD4368	Phase 2
0.7117	Intermediate Similarity	NPD6995	Phase 1
0.7108	Intermediate Similarity	NPD2383	Phase 1
0.7103	Intermediate Similarity	NPD7222	Phase 2
0.7097	Intermediate Similarity	NPD8093	Discontinued
0.7095	Intermediate Similarity	NPD8395	Approved
0.7095	Intermediate Similarity	NPD8396	Approved
0.7093	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8115	Approved
0.7089	Intermediate Similarity	NPD8114	Approved
0.7081	Intermediate Similarity	NPD5003	Discontinued
0.7079	Intermediate Similarity	NPD3319	Phase 1
0.7079	Intermediate Similarity	NPD3320	Approved
0.7079	Intermediate Similarity	NPD3318	Approved
0.7078	Intermediate Similarity	NPD3389	Approved
0.7078	Intermediate Similarity	NPD3394	Approved
0.7078	Intermediate Similarity	NPD3393	Approved
0.7073	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD750	Phase 2
0.707	Intermediate Similarity	NPD2509	Approved
0.707	Intermediate Similarity	NPD2510	Approved
0.707	Intermediate Similarity	NPD7665	Phase 2
0.707	Intermediate Similarity	NPD7666	Phase 3
0.7064	Intermediate Similarity	NPD8102	Discontinued
0.7062	Intermediate Similarity	NPD4501	Approved
0.7062	Intermediate Similarity	NPD4500	Approved
0.7061	Intermediate Similarity	NPD4373	Phase 2
0.7053	Intermediate Similarity	NPD6665	Discontinued
0.7048	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6176	Phase 1
0.7039	Intermediate Similarity	NPD4499	Approved
0.7032	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4203	Approved
0.703	Intermediate Similarity	NPD4204	Approved
0.7028	Intermediate Similarity	NPD7817	Phase 1
0.7028	Intermediate Similarity	NPD7727	Phase 2
0.7026	Intermediate Similarity	NPD5140	Approved
0.7026	Intermediate Similarity	NPD5138	Approved
0.7018	Intermediate Similarity	NPD7797	Approved
0.7018	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7796	Approved
0.7015	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4429	Discontinued
0.7014	Intermediate Similarity	NPD3814	Phase 1
0.701	Intermediate Similarity	NPD2762	Phase 2
0.7009	Intermediate Similarity	NPD4795	Phase 2
0.7004	Intermediate Similarity	NPD4952	Phase 3
0.7	Intermediate Similarity	NPD1544	Phase 1
0.6996	Remote Similarity	NPD6456	Discontinued
0.6995	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7618	Phase 3
0.6986	Remote Similarity	NPD3945	Discontinued
0.6986	Remote Similarity	NPD7619	Phase 3
0.6986	Remote Similarity	NPD4418	Discontinued
0.6986	Remote Similarity	NPD8094	Discontinued
0.6983	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8016	Phase 3
0.6982	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1739	Approved
0.6981	Remote Similarity	NPD1740	Approved
0.6981	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5488	Discontinued
0.6977	Remote Similarity	NPD3003	Approved
0.6977	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5936	Approved
0.6972	Remote Similarity	NPD5939	Approved
0.697	Remote Similarity	NPD1573	Approved
0.697	Remote Similarity	NPD1575	Approved
0.697	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6159	Phase 2
0.6957	Remote Similarity	NPD2564	Approved
0.6957	Remote Similarity	NPD2565	Phase 2
0.6955	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6790	Phase 1
0.6953	Remote Similarity	NPD8349	Phase 1
0.695	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7452	Approved
0.6944	Remote Similarity	NPD6290	Phase 2
0.6944	Remote Similarity	NPD7453	Approved
0.6942	Remote Similarity	NPD7708	Approved
0.6941	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1631	Approved
0.6937	Remote Similarity	NPD3354	Phase 2
0.6934	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1768	Approved
0.6932	Remote Similarity	NPD7181	Phase 3
0.6929	Remote Similarity	NPD8091	Phase 3
0.6927	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7853	Phase 2
0.6923	Remote Similarity	NPD6716	Phase 1
0.6923	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7112	Discontinued
0.6912	Remote Similarity	NPD2189	Approved
0.6912	Remote Similarity	NPD2187	Approved
0.691	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4561	Discontinued
0.6909	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1534	Approved
0.6905	Remote Similarity	NPD4602	Approved
0.6905	Remote Similarity	NPD4400	Approved
0.6903	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6732	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data