NPASS Compound

Structure

NPC475962 OpenBabel07101718322D 27 31 0 0 1 0 0 0 0 0999 V2000 -2.9033 -0.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6006 -1.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2660 2.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1856 2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9341 1.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 1.1442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 2.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9393 0.0007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7374 1.9332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6878 0.9685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2447 1.5172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2512 0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 0.7642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0662 2.5012 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.2270 -0.7011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2306 0.2185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5337 2.4637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9362 -0.9323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 1 1 1 0 0 0 12 24 1 0 0 0 0 13 9 1 1 0 0 0 14 12 1 6 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 1 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 19 1 6 0 0 0 21 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.19
Volume:	372.962
LogP:	1.459
LogD:	1.834
LogS:	-3.274
# Rotatable Bonds:	3
TPSA:	82.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	5.692
Fsp3:	0.619
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:	-5.429
MDCK Permeability:	2.3199494535219856e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916
Plasma Protein Binding (PPB):	59.056060791015625%
Volume Distribution (VD):	3.819
Pgp-substrate:	50.57331466674805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.765
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.795

ADMET: Excretion

Clearance (CL):	5.774
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.11
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC475962

Natural Product ID:	NPC475962
*Common Name:**	Heyneanine Hydroxyindolenine
IUPAC Name:	n.a.
Synonyms:	Heyneanine Hydroxyindolenine
Standard InCHIKey:	BPKMKKDJAWRIOB-JBEOEGFRSA-N
Standard InCHI:	InChI=1S/C21H26N2O4/c1-12(24)14-9-13-10-20(19(25)27-2)17(14)23(11-13)8-7-21(26)15-5-3-4-6-16(15)22-18(20)21/h3-6,12-14,17,24,26H,7-11H2,1-2H3/t12-,13-,14+,17-,20-,21+/m0/s1
SMILES:	C[C@@H]([C@H]1C[C@H]2C[C@@]3([C@H]1N(CC[C@]1(c4ccccc4N=C31)O)C2)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519744
PubChem CID:	44559830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type 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
NPO31010	Ervatamia hainanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20850311]
NPO41061	Ervatamia coronaria var. plena	Strain	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404150]
NPO31010	Ervatamia hainanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	1000000.0	nM	PMID[493243]

☑ 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 NPC475962 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	225
0.1-0.2	1019
0.2-0.3	2678
0.3-0.4	9496
0.4-0.5	21286
0.5-0.6	6729
0.6-0.7	1166
0.7-0.8	89
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC278887
0.8994	High Similarity	NPC474077
0.8547	High Similarity	NPC203972
0.8266	Intermediate Similarity	NPC210415
0.8266	Intermediate Similarity	NPC293255
0.8266	Intermediate Similarity	NPC298851
0.8266	Intermediate Similarity	NPC21752
0.8266	Intermediate Similarity	NPC181138
0.8266	Intermediate Similarity	NPC276993
0.8	Intermediate Similarity	NPC211525
0.8	Intermediate Similarity	NPC153694
0.7956	Intermediate Similarity	NPC469460
0.7892	Intermediate Similarity	NPC472100
0.7886	Intermediate Similarity	NPC469462
0.7874	Intermediate Similarity	NPC470069
0.7874	Intermediate Similarity	NPC52059
0.7849	Intermediate Similarity	NPC243673
0.7849	Intermediate Similarity	NPC310403
0.7849	Intermediate Similarity	NPC148468
0.7849	Intermediate Similarity	NPC263709
0.7849	Intermediate Similarity	NPC63210
0.7849	Intermediate Similarity	NPC97380
0.7814	Intermediate Similarity	NPC291759
0.776	Intermediate Similarity	NPC133591
0.7717	Intermediate Similarity	NPC38823
0.7717	Intermediate Similarity	NPC207033
0.7674	Intermediate Similarity	NPC161827
0.7663	Intermediate Similarity	NPC472209
0.7647	Intermediate Similarity	NPC28510
0.763	Intermediate Similarity	NPC477157
0.763	Intermediate Similarity	NPC477156
0.7622	Intermediate Similarity	NPC282092
0.7572	Intermediate Similarity	NPC473297
0.7539	Intermediate Similarity	NPC475559
0.7514	Intermediate Similarity	NPC245741
0.7458	Intermediate Similarity	NPC472121
0.743	Intermediate Similarity	NPC472115
0.743	Intermediate Similarity	NPC472114
0.7401	Intermediate Similarity	NPC477158
0.7358	Intermediate Similarity	NPC302548
0.7353	Intermediate Similarity	NPC472103
0.7326	Intermediate Similarity	NPC97584
0.7322	Intermediate Similarity	NPC13367
0.7303	Intermediate Similarity	NPC474058
0.7297	Intermediate Similarity	NPC218594
0.7297	Intermediate Similarity	NPC99043
0.7283	Intermediate Similarity	NPC476441
0.7263	Intermediate Similarity	NPC472101
0.7263	Intermediate Similarity	NPC472120
0.7189	Intermediate Similarity	NPC129624
0.7189	Intermediate Similarity	NPC203202
0.7189	Intermediate Similarity	NPC264482
0.7188	Intermediate Similarity	NPC25401
0.7151	Intermediate Similarity	NPC469461
0.715	Intermediate Similarity	NPC473105
0.712	Intermediate Similarity	NPC14994
0.7118	Intermediate Similarity	NPC243162
0.711	Intermediate Similarity	NPC116519
0.7103	Intermediate Similarity	NPC475720
0.7103	Intermediate Similarity	NPC474192
0.7088	Intermediate Similarity	NPC472106
0.7081	Intermediate Similarity	NPC476425
0.7072	Intermediate Similarity	NPC472117
0.7059	Intermediate Similarity	NPC186669
0.7047	Intermediate Similarity	NPC22689
0.7047	Intermediate Similarity	NPC105055
0.7039	Intermediate Similarity	NPC29285
0.7037	Intermediate Similarity	NPC476428
0.7021	Intermediate Similarity	NPC6974
0.7017	Intermediate Similarity	NPC143457
0.7	Intermediate Similarity	NPC1464
0.7	Intermediate Similarity	NPC159963
0.7	Intermediate Similarity	NPC477159
0.6985	Remote Similarity	NPC475489
0.6973	Remote Similarity	NPC469915
0.6967	Remote Similarity	NPC106593
0.695	Remote Similarity	NPC471512
0.6943	Remote Similarity	NPC472323
0.6931	Remote Similarity	NPC472331
0.6931	Remote Similarity	NPC126515
0.6931	Remote Similarity	NPC274002
0.6927	Remote Similarity	NPC478076
0.6923	Remote Similarity	NPC469928
0.6919	Remote Similarity	NPC90967
0.6909	Remote Similarity	NPC475816
0.6907	Remote Similarity	NPC217294
0.6895	Remote Similarity	NPC39822
0.689	Remote Similarity	NPC317758
0.6888	Remote Similarity	NPC204970
0.6885	Remote Similarity	NPC476231
0.6884	Remote Similarity	NPC102008
0.6884	Remote Similarity	NPC33949
0.6872	Remote Similarity	NPC140311
0.6872	Remote Similarity	NPC329858
0.6868	Remote Similarity	NPC471122
0.6854	Remote Similarity	NPC473667
0.6851	Remote Similarity	NPC217801
0.6847	Remote Similarity	NPC14339
0.6847	Remote Similarity	NPC87714
0.6842	Remote Similarity	NPC321211
0.6842	Remote Similarity	NPC330009
0.6831	Remote Similarity	NPC472102
0.6831	Remote Similarity	NPC309531
0.6831	Remote Similarity	NPC225319
0.6818	Remote Similarity	NPC328824
0.6814	Remote Similarity	NPC246140
0.6814	Remote Similarity	NPC195787
0.6813	Remote Similarity	NPC113946
0.6809	Remote Similarity	NPC96901
0.6789	Remote Similarity	NPC476326
0.6786	Remote Similarity	NPC471195
0.6786	Remote Similarity	NPC314333
0.6786	Remote Similarity	NPC473298
0.6786	Remote Similarity	NPC471196
0.6784	Remote Similarity	NPC108804
0.6784	Remote Similarity	NPC476218
0.6782	Remote Similarity	NPC472329
0.6782	Remote Similarity	NPC472330
0.6779	Remote Similarity	NPC475778
0.6779	Remote Similarity	NPC292517
0.6776	Remote Similarity	NPC36495
0.6769	Remote Similarity	NPC21425
0.6769	Remote Similarity	NPC181928
0.6763	Remote Similarity	NPC234999
0.6762	Remote Similarity	NPC234772
0.6762	Remote Similarity	NPC30570
0.6757	Remote Similarity	NPC313757
0.6744	Remote Similarity	NPC477394
0.6739	Remote Similarity	NPC201424
0.6734	Remote Similarity	NPC476205
0.6734	Remote Similarity	NPC476207
0.6734	Remote Similarity	NPC476256
0.6734	Remote Similarity	NPC476129
0.6734	Remote Similarity	NPC476257
0.6734	Remote Similarity	NPC259791
0.6734	Remote Similarity	NPC476206
0.6734	Remote Similarity	NPC476212
0.673	Remote Similarity	NPC473837
0.672	Remote Similarity	NPC139085
0.672	Remote Similarity	NPC251212
0.672	Remote Similarity	NPC214626
0.672	Remote Similarity	NPC471124
0.6719	Remote Similarity	NPC15840
0.6716	Remote Similarity	NPC112752
0.6716	Remote Similarity	NPC311054
0.6715	Remote Similarity	NPC477160
0.6714	Remote Similarity	NPC189661
0.6703	Remote Similarity	NPC282339
0.6703	Remote Similarity	NPC99632
0.6703	Remote Similarity	NPC176983
0.6685	Remote Similarity	NPC235460
0.6682	Remote Similarity	NPC473458
0.6667	Remote Similarity	NPC223590
0.6667	Remote Similarity	NPC473007
0.6667	Remote Similarity	NPC52262
0.6667	Remote Similarity	NPC313663
0.6667	Remote Similarity	NPC322621
0.6667	Remote Similarity	NPC472097
0.665	Remote Similarity	NPC221687
0.665	Remote Similarity	NPC34717
0.665	Remote Similarity	NPC284706
0.6649	Remote Similarity	NPC223595
0.6649	Remote Similarity	NPC167724
0.6649	Remote Similarity	NPC248117
0.6649	Remote Similarity	NPC98197
0.6649	Remote Similarity	NPC224970
0.6648	Remote Similarity	NPC476757
0.6648	Remote Similarity	NPC94602
0.6647	Remote Similarity	NPC183722
0.6635	Remote Similarity	NPC168250
0.6634	Remote Similarity	NPC52557
0.6632	Remote Similarity	NPC11149
0.663	Remote Similarity	NPC61013
0.6618	Remote Similarity	NPC176371
0.6618	Remote Similarity	NPC475835
0.6618	Remote Similarity	NPC136573
0.6616	Remote Similarity	NPC174629
0.6616	Remote Similarity	NPC473008
0.6616	Remote Similarity	NPC5630
0.6615	Remote Similarity	NPC472119
0.6614	Remote Similarity	NPC257354
0.6613	Remote Similarity	NPC85651
0.6602	Remote Similarity	NPC185742
0.6602	Remote Similarity	NPC475847
0.6601	Remote Similarity	NPC90358
0.6601	Remote Similarity	NPC107828
0.6599	Remote Similarity	NPC473815
0.6595	Remote Similarity	NPC193410
0.6588	Remote Similarity	NPC69496
0.6585	Remote Similarity	NPC162730
0.6583	Remote Similarity	NPC203628
0.6578	Remote Similarity	NPC189116
0.6576	Remote Similarity	NPC93343
0.6575	Remote Similarity	NPC311906
0.6573	Remote Similarity	NPC262216
0.6573	Remote Similarity	NPC162812
0.6569	Remote Similarity	NPC312870
0.6569	Remote Similarity	NPC199851
0.6569	Remote Similarity	NPC294909
0.6569	Remote Similarity	NPC254240

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 NPC475962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	472
0.2-0.3	707
0.3-0.4	1448
0.4-0.5	3515
0.5-0.6	2554
0.6-0.7	308
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7111	Intermediate Similarity	NPD7600	Phase 2
0.7056	Intermediate Similarity	NPD7599	Phase 2
0.6914	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7778	Approved
0.6884	Remote Similarity	NPD53	Approved
0.6884	Remote Similarity	NPD7777	Approved
0.6833	Remote Similarity	NPD4120	Approved
0.6833	Remote Similarity	NPD4121	Phase 3
0.6824	Remote Similarity	NPD5182	Approved
0.6824	Remote Similarity	NPD5185	Approved
0.6824	Remote Similarity	NPD5184	Approved
0.6796	Remote Similarity	NPD5742	Approved
0.6796	Remote Similarity	NPD5743	Approved
0.6796	Remote Similarity	NPD5741	Approved
0.6786	Remote Similarity	NPD4499	Approved
0.673	Remote Similarity	NPD8326	Phase 3
0.673	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8325	Phase 3
0.6704	Remote Similarity	NPD4682	Phase 2
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD7715	Approved
0.6615	Remote Similarity	NPD6641	Approved
0.6615	Remote Similarity	NPD6642	Approved
0.6615	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7795	Phase 2
0.6595	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2613	Approved
0.6573	Remote Similarity	NPD2575	Approved
0.6569	Remote Similarity	NPD4500	Approved
0.6569	Remote Similarity	NPD4501	Approved
0.6552	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6874	Approved
0.6519	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4951	Discontinued
0.6515	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3422	Phase 3
0.651	Remote Similarity	NPD3423	Phase 2
0.6505	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4601	Approved
0.6488	Remote Similarity	NPD4600	Approved
0.6486	Remote Similarity	NPD6913	Approved
0.648	Remote Similarity	NPD2387	Approved
0.6474	Remote Similarity	NPD4746	Phase 3
0.6474	Remote Similarity	NPD3090	Approved
0.6474	Remote Similarity	NPD3087	Approved
0.6474	Remote Similarity	NPD3614	Approved
0.6474	Remote Similarity	NPD2573	Approved
0.6474	Remote Similarity	NPD2570	Approved
0.6474	Remote Similarity	NPD3615	Approved
0.6474	Remote Similarity	NPD3088	Approved
0.6474	Remote Similarity	NPD2566	Approved
0.6474	Remote Similarity	NPD4745	Approved
0.6474	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2574	Discontinued
0.6474	Remote Similarity	NPD3089	Approved
0.6474	Remote Similarity	NPD3616	Approved
0.6474	Remote Similarity	NPD2571	Approved
0.6468	Remote Similarity	NPD7570	Approved
0.6468	Remote Similarity	NPD7569	Approved
0.6462	Remote Similarity	NPD5899	Approved
0.6462	Remote Similarity	NPD5898	Approved
0.6462	Remote Similarity	NPD5897	Approved
0.6455	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5119	Approved
0.6437	Remote Similarity	NPD5121	Approved
0.6437	Remote Similarity	NPD5120	Approved
0.6418	Remote Similarity	NPD5076	Approved
0.6418	Remote Similarity	NPD5077	Approved
0.6412	Remote Similarity	NPD2627	Approved
0.6412	Remote Similarity	NPD2159	Approved
0.6412	Remote Similarity	NPD2628	Approved
0.6412	Remote Similarity	NPD2625	Approved
0.6412	Remote Similarity	NPD2626	Approved
0.6412	Remote Similarity	NPD2160	Approved
0.6406	Remote Similarity	NPD3824	Phase 1
0.6406	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4602	Approved
0.64	Remote Similarity	NPD4684	Phase 3
0.64	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4685	Phase 3
0.64	Remote Similarity	NPD8025	Phase 2
0.64	Remote Similarity	NPD4686	Approved
0.6389	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8146	Phase 2
0.6386	Remote Similarity	NPD2212	Approved
0.6386	Remote Similarity	NPD2210	Approved
0.6384	Remote Similarity	NPD3170	Approved
0.6378	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5811	Approved
0.6373	Remote Similarity	NPD43	Approved
0.6373	Remote Similarity	NPD6182	Approved
0.6373	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2612	Approved
0.6369	Remote Similarity	NPD2608	Approved
0.6369	Remote Similarity	NPD4216	Approved
0.6369	Remote Similarity	NPD4215	Approved
0.6369	Remote Similarity	NPD2611	Approved
0.6369	Remote Similarity	NPD3132	Approved
0.6369	Remote Similarity	NPD2609	Approved
0.6369	Remote Similarity	NPD4217	Approved
0.6369	Remote Similarity	NPD3131	Approved
0.6369	Remote Similarity	NPD2610	Approved
0.6369	Remote Similarity	NPD4218	Approved
0.6364	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4738	Phase 2
0.6354	Remote Similarity	NPD7295	Approved
0.6353	Remote Similarity	NPD6325	Discontinued
0.6343	Remote Similarity	NPD6310	Approved
0.6343	Remote Similarity	NPD6311	Approved
0.6343	Remote Similarity	NPD6309	Approved
0.6339	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5823	Approved
0.633	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5190	Phase 2
0.6321	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7962	Phase 2
0.6313	Remote Similarity	NPD7878	Phase 2
0.6313	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3067	Approved
0.6308	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD2844	Phase 3
0.6301	Remote Similarity	NPD5201	Approved
0.6301	Remote Similarity	NPD5203	Approved
0.6301	Remote Similarity	NPD4617	Approved
0.6301	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4620	Approved
0.6298	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6878	Phase 2
0.6294	Remote Similarity	NPD6879	Phase 2
0.6294	Remote Similarity	NPD5157	Phase 1
0.6294	Remote Similarity	NPD5159	Phase 2
0.629	Remote Similarity	NPD1634	Approved
0.6286	Remote Similarity	NPD1594	Phase 3
0.6286	Remote Similarity	NPD1595	Approved
0.6283	Remote Similarity	NPD7036	Phase 3
0.6283	Remote Similarity	NPD7035	Approved
0.6278	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7011	Discontinued
0.6277	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4603	Phase 2
0.6269	Remote Similarity	NPD4948	Discontinued
0.6268	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4275	Approved
0.6264	Remote Similarity	NPD3720	Discontinued
0.6264	Remote Similarity	NPD4274	Approved
0.6262	Remote Similarity	NPD5003	Discontinued
0.6257	Remote Similarity	NPD5578	Approved
0.6257	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1036	Approved
0.6257	Remote Similarity	NPD6320	Approved
0.6256	Remote Similarity	NPD5466	Approved
0.6256	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5042	Phase 1
0.625	Remote Similarity	NPD4432	Discontinued
0.625	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5942	Approved
0.625	Remote Similarity	NPD5941	Approved
0.6244	Remote Similarity	NPD4427	Phase 2
0.6238	Remote Similarity	NPD7205	Discontinued
0.6237	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD1633	Approved
0.6236	Remote Similarity	NPD2670	Approved
0.6236	Remote Similarity	NPD2569	Approved
0.6236	Remote Similarity	NPD2567	Approved
0.6232	Remote Similarity	NPD5856	Discontinued
0.6231	Remote Similarity	NPD5596	Phase 2
0.6229	Remote Similarity	NPD4621	Approved
0.6229	Remote Similarity	NPD4619	Approved
0.6224	Remote Similarity	NPD2381	Approved
0.6224	Remote Similarity	NPD2380	Approved
0.6224	Remote Similarity	NPD2382	Approved
0.6223	Remote Similarity	NPD6276	Discontinued
0.6223	Remote Similarity	NPD7105	Phase 1
0.6223	Remote Similarity	NPD2672	Discontinued
0.6216	Remote Similarity	NPD7613	Discontinued
0.6207	Remote Similarity	NPD8361	Approved
0.6207	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8360	Approved
0.6207	Remote Similarity	NPD2565	Phase 2
0.6207	Remote Similarity	NPD2564	Approved
0.6205	Remote Similarity	NPD5997	Discontinued
0.6198	Remote Similarity	NPD5430	Discontinued
0.619	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6483	Approved
0.6188	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6484	Approved
0.6184	Remote Similarity	NPD8485	Approved
0.6184	Remote Similarity	NPD7238	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