NPASS Compound

Structure

CID11149 OpenBabel06191715342D 28 32 0 0 1 0 0 0 0 0999 V2000 -3.4736 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7966 4.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7130 1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6178 2.5795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6178 1.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7984 3.0525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7985 1.1596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0836 3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5639 3.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2997 2.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7805 2.9526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4803 0.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7803 2.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2997 1.6325 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4803 1.1594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9786 2.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9787 1.6327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4804 3.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3395 1.6326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1594 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6792 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3394 2.5793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3001 3.5254 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1593 1.1595 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4805 4.8416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0765 0.1005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0591 -0.9170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 3 13 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 9 1 0 0 0 0 9 23 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 14 10 1 1 0 0 0 14 15 1 0 0 0 0 15 12 1 6 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 1 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.19
Volume:	387.622
LogP:	1.582
LogD:	1.639
LogS:	-2.863
# Rotatable Bonds:	0
TPSA:	70.08
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	6.249
Fsp3:	0.545
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:	-4.921
MDCK Permeability:	2.8736705644405447e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.664
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.697

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	51.52892303466797%
Volume Distribution (VD):	0.986
Pgp-substrate:	65.09076690673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.137
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.896

ADMET: Excretion

Clearance (CL):	8.084
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.388
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.444
Carcinogencity:	0.598
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC11149

Natural Product ID:	NPC11149
*Common Name:**	Holstiine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BLJOXWGKDCMTMU-PGBKOQGOSA-N
Standard InCHI:	InChI=1S/C22H26N2O4/c1-3-13-11-23(2)9-8-22-16-6-4-5-7-17(16)24-19(22)15(14(13)10-18(22)25)12-28-21(27)20(24)26/h3-7,14-15,19,21,27H,8-12H2,1-2H3/b13-3-/t14-,15+,19-,21-,22+/m0/s1
SMILES:	C/C=C1/CN(C)CC[C@@]23C(=O)C[C@@H]1[C@H]1CO[C@@H](C(=O)N([C@H]21)c1c3cccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2262631
PubChem CID:	23278454
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO3878	Strychnos holstii	Species	Loganiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	24.83	ug.mL-1	PMID[452904]

☑ 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 NPC11149 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	234
0.1-0.2	1187
0.2-0.3	4276
0.3-0.4	22689
0.4-0.5	10835
0.5-0.6	3036
0.6-0.7	410
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8314	Intermediate Similarity	NPC96901
0.7836	Intermediate Similarity	NPC113946
0.7543	Intermediate Similarity	NPC225319
0.7543	Intermediate Similarity	NPC315368
0.7514	Intermediate Similarity	NPC472106
0.75	Intermediate Similarity	NPC472101
0.75	Intermediate Similarity	NPC472120
0.7472	Intermediate Similarity	NPC279527
0.7472	Intermediate Similarity	NPC214960
0.7471	Intermediate Similarity	NPC29285
0.7443	Intermediate Similarity	NPC472102
0.7443	Intermediate Similarity	NPC309531
0.7403	Intermediate Similarity	NPC139085
0.7403	Intermediate Similarity	NPC214626
0.7403	Intermediate Similarity	NPC251212
0.7403	Intermediate Similarity	NPC285622
0.7401	Intermediate Similarity	NPC472117
0.7394	Intermediate Similarity	NPC284706
0.7345	Intermediate Similarity	NPC201424
0.7292	Intermediate Similarity	NPC221687
0.7263	Intermediate Similarity	NPC473298
0.7262	Intermediate Similarity	NPC315051
0.7254	Intermediate Similarity	NPC473375
0.7254	Intermediate Similarity	NPC97100
0.7228	Intermediate Similarity	NPC129624
0.7219	Intermediate Similarity	NPC477159
0.7207	Intermediate Similarity	NPC99632
0.7207	Intermediate Similarity	NPC286871
0.7207	Intermediate Similarity	NPC282339
0.7194	Intermediate Similarity	NPC475489
0.7157	Intermediate Similarity	NPC471512
0.7151	Intermediate Similarity	NPC474058
0.7151	Intermediate Similarity	NPC321211
0.7143	Intermediate Similarity	NPC52262
0.7143	Intermediate Similarity	NPC322621
0.7111	Intermediate Similarity	NPC176983
0.7097	Intermediate Similarity	NPC260075
0.7083	Intermediate Similarity	NPC22689
0.7083	Intermediate Similarity	NPC105055
0.7069	Intermediate Similarity	NPC212799
0.7056	Intermediate Similarity	NPC143457
0.7041	Intermediate Similarity	NPC90967
0.7039	Intermediate Similarity	NPC104345
0.7011	Intermediate Similarity	NPC469915
0.7	Intermediate Similarity	NPC245741
0.6989	Remote Similarity	NPC13367
0.6979	Remote Similarity	NPC181928
0.6976	Remote Similarity	NPC10732
0.6966	Remote Similarity	NPC478076
0.6927	Remote Similarity	NPC282092
0.6911	Remote Similarity	NPC97584
0.6902	Remote Similarity	NPC472114
0.6902	Remote Similarity	NPC472115
0.6891	Remote Similarity	NPC14994
0.6882	Remote Similarity	NPC355
0.6881	Remote Similarity	NPC329833
0.6875	Remote Similarity	NPC259626
0.6869	Remote Similarity	NPC162440
0.6869	Remote Similarity	NPC470480
0.6862	Remote Similarity	NPC476441
0.6853	Remote Similarity	NPC34717
0.6848	Remote Similarity	NPC52059
0.6848	Remote Similarity	NPC470069
0.6845	Remote Similarity	NPC476425
0.6823	Remote Similarity	NPC2933
0.6818	Remote Similarity	NPC264589
0.6812	Remote Similarity	NPC470481
0.6812	Remote Similarity	NPC470482
0.6793	Remote Similarity	NPC313757
0.6789	Remote Similarity	NPC99043
0.6789	Remote Similarity	NPC475094
0.6789	Remote Similarity	NPC218594
0.6789	Remote Similarity	NPC6974
0.6774	Remote Similarity	NPC224970
0.6774	Remote Similarity	NPC167724
0.6774	Remote Similarity	NPC223595
0.6772	Remote Similarity	NPC203202
0.6772	Remote Similarity	NPC264482
0.6771	Remote Similarity	NPC256288
0.6771	Remote Similarity	NPC159963
0.6758	Remote Similarity	NPC153694
0.6758	Remote Similarity	NPC211525
0.6757	Remote Similarity	NPC471124
0.6739	Remote Similarity	NPC293458
0.6738	Remote Similarity	NPC472118
0.6737	Remote Similarity	NPC186669
0.6724	Remote Similarity	NPC186284
0.6724	Remote Similarity	NPC22082
0.6721	Remote Similarity	NPC63210
0.6721	Remote Similarity	NPC148468
0.6721	Remote Similarity	NPC263709
0.6721	Remote Similarity	NPC97380
0.6721	Remote Similarity	NPC471122
0.6721	Remote Similarity	NPC243673
0.6721	Remote Similarity	NPC310403
0.672	Remote Similarity	NPC278887
0.6701	Remote Similarity	NPC25401
0.67	Remote Similarity	NPC475559
0.67	Remote Similarity	NPC302548
0.6685	Remote Similarity	NPC248117
0.6685	Remote Similarity	NPC73644
0.6683	Remote Similarity	NPC138830
0.6683	Remote Similarity	NPC67904
0.6667	Remote Similarity	NPC473615
0.6667	Remote Similarity	NPC100863
0.6649	Remote Similarity	NPC472121
0.6648	Remote Similarity	NPC161827
0.6648	Remote Similarity	NPC473297
0.6633	Remote Similarity	NPC229484
0.6632	Remote Similarity	NPC476428
0.6632	Remote Similarity	NPC475962
0.663	Remote Similarity	NPC36495
0.663	Remote Similarity	NPC193410
0.6628	Remote Similarity	NPC76785
0.6628	Remote Similarity	NPC475318
0.6628	Remote Similarity	NPC49577
0.6628	Remote Similarity	NPC476102
0.6628	Remote Similarity	NPC9687
0.6628	Remote Similarity	NPC474811
0.6628	Remote Similarity	NPC475598
0.6628	Remote Similarity	NPC260045
0.6628	Remote Similarity	NPC79465
0.6628	Remote Similarity	NPC118099
0.6628	Remote Similarity	NPC474855
0.6628	Remote Similarity	NPC90194
0.6628	Remote Similarity	NPC273907
0.6628	Remote Similarity	NPC474787
0.6628	Remote Similarity	NPC151706
0.6628	Remote Similarity	NPC293377
0.6599	Remote Similarity	NPC292675
0.6595	Remote Similarity	NPC68650
0.6591	Remote Similarity	NPC471516
0.6583	Remote Similarity	NPC473004
0.6579	Remote Similarity	NPC298851
0.6579	Remote Similarity	NPC181138
0.6579	Remote Similarity	NPC473743
0.6579	Remote Similarity	NPC276993
0.6579	Remote Similarity	NPC21752
0.6579	Remote Similarity	NPC293255
0.6579	Remote Similarity	NPC210415
0.6576	Remote Similarity	NPC61013
0.6576	Remote Similarity	NPC123241
0.6575	Remote Similarity	NPC475763
0.6575	Remote Similarity	NPC66936
0.6571	Remote Similarity	NPC243162
0.6562	Remote Similarity	NPC476326
0.6556	Remote Similarity	NPC242000
0.6554	Remote Similarity	NPC209509
0.6545	Remote Similarity	NPC469726
0.6545	Remote Similarity	NPC329338
0.6542	Remote Similarity	NPC288110
0.6537	Remote Similarity	NPC162730
0.6534	Remote Similarity	NPC470301
0.651	Remote Similarity	NPC475427
0.6495	Remote Similarity	NPC15840
0.6494	Remote Similarity	NPC471123
0.6493	Remote Similarity	NPC475778
0.6492	Remote Similarity	NPC177261
0.6492	Remote Similarity	NPC307640
0.6482	Remote Similarity	NPC329858
0.6479	Remote Similarity	NPC234772
0.6477	Remote Similarity	NPC269398
0.6477	Remote Similarity	NPC263493
0.6471	Remote Similarity	NPC469741
0.6471	Remote Similarity	NPC476231
0.6465	Remote Similarity	NPC472323
0.6465	Remote Similarity	NPC222046
0.6465	Remote Similarity	NPC21425
0.6461	Remote Similarity	NPC5620
0.6458	Remote Similarity	NPC470548
0.6456	Remote Similarity	NPC474116
0.6447	Remote Similarity	NPC473007
0.6444	Remote Similarity	NPC470579
0.6436	Remote Similarity	NPC243626
0.6436	Remote Similarity	NPC230313
0.6429	Remote Similarity	NPC469743
0.6429	Remote Similarity	NPC477160
0.6425	Remote Similarity	NPC311330
0.6422	Remote Similarity	NPC149708
0.642	Remote Similarity	NPC469560
0.6419	Remote Similarity	NPC77777
0.641	Remote Similarity	NPC286994
0.6409	Remote Similarity	NPC473458
0.6406	Remote Similarity	NPC473880
0.64	Remote Similarity	NPC314333
0.64	Remote Similarity	NPC473008
0.64	Remote Similarity	NPC474059
0.64	Remote Similarity	NPC471264
0.64	Remote Similarity	NPC471265
0.6398	Remote Similarity	NPC234999
0.6394	Remote Similarity	NPC268077
0.6393	Remote Similarity	NPC314223
0.6393	Remote Similarity	NPC477394
0.6392	Remote Similarity	NPC474081
0.6386	Remote Similarity	NPC470485
0.6383	Remote Similarity	NPC253667
0.6383	Remote Similarity	NPC35510
0.6382	Remote Similarity	NPC285841
0.6382	Remote Similarity	NPC473815
0.6378	Remote Similarity	NPC113626

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 NPC11149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	505
0.2-0.3	798
0.3-0.4	2031
0.4-0.5	3819
0.5-0.6	1716
0.6-0.7	113
0.7-0.8	4
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
0.7443	Intermediate Similarity	NPD7600	Phase 2
0.7386	Intermediate Similarity	NPD7599	Phase 2
0.7326	Intermediate Similarity	NPD5942	Approved
0.7326	Intermediate Similarity	NPD5941	Approved
0.7039	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7587	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5024	Approved
0.69	Remote Similarity	NPD6238	Discontinued
0.6889	Remote Similarity	NPD1663	Discontinued
0.6854	Remote Similarity	NPD7606	Phase 3
0.6839	Remote Similarity	NPD2820	Phase 3
0.6782	Remote Similarity	NPD2365	Approved
0.678	Remote Similarity	NPD7478	Approved
0.6724	Remote Similarity	NPD2093	Discontinued
0.6718	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7487	Discontinued
0.6703	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7295	Approved
0.6648	Remote Similarity	NPD7082	Approved
0.6648	Remote Similarity	NPD4432	Discontinued
0.6614	Remote Similarity	NPD5633	Discontinued
0.6598	Remote Similarity	NPD7962	Phase 2
0.6571	Remote Similarity	NPD7511	Approved
0.6571	Remote Similarity	NPD7512	Approved
0.6522	Remote Similarity	NPD7105	Phase 1
0.6513	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6768	Approved
0.6494	Remote Similarity	NPD6073	Approved
0.6494	Remote Similarity	NPD7510	Approved
0.6488	Remote Similarity	NPD6792	Phase 3
0.6488	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.644	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6805	Discontinued
0.6425	Remote Similarity	NPD7259	Approved
0.6425	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2790	Discontinued
0.6409	Remote Similarity	NPD8165	Discontinued
0.6407	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6566	Discontinued
0.6402	Remote Similarity	NPD5991	Approved
0.6402	Remote Similarity	NPD5990	Approved
0.64	Remote Similarity	NPD4499	Approved
0.6398	Remote Similarity	NPD8630	Approved
0.6379	Remote Similarity	NPD5182	Approved
0.6379	Remote Similarity	NPD5184	Approved
0.6379	Remote Similarity	NPD5185	Approved
0.6374	Remote Similarity	NPD4682	Phase 2
0.6373	Remote Similarity	NPD5466	Approved
0.6369	Remote Similarity	NPD519	Approved
0.6369	Remote Similarity	NPD4430	Phase 2
0.6364	Remote Similarity	NPD6345	Approved
0.6364	Remote Similarity	NPD6343	Approved
0.6349	Remote Similarity	NPD3790	Phase 2
0.6341	Remote Similarity	NPD6069	Approved
0.6341	Remote Similarity	NPD6070	Approved
0.6327	Remote Similarity	NPD6878	Phase 2
0.6327	Remote Similarity	NPD6879	Phase 2
0.6324	Remote Similarity	NPD4121	Phase 3
0.6324	Remote Similarity	NPD4120	Approved
0.6321	Remote Similarity	NPD5997	Discontinued
0.6316	Remote Similarity	NPD5993	Phase 1
0.6311	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD7795	Phase 2
0.63	Remote Similarity	NPD6484	Approved
0.63	Remote Similarity	NPD6483	Approved
0.6298	Remote Similarity	NPD6017	Discontinued
0.629	Remote Similarity	NPD5742	Approved
0.629	Remote Similarity	NPD5741	Approved
0.629	Remote Similarity	NPD5743	Approved
0.6289	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6659	Phase 2
0.6283	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4175	Approved
0.6279	Remote Similarity	NPD4177	Approved
0.6278	Remote Similarity	NPD7824	Approved
0.6275	Remote Similarity	NPD4602	Approved
0.6272	Remote Similarity	NPD2584	Suspended
0.6271	Remote Similarity	NPD6295	Approved
0.6271	Remote Similarity	NPD6342	Discontinued
0.6271	Remote Similarity	NPD6294	Approved
0.6264	Remote Similarity	NPD3141	Discontinued
0.6264	Remote Similarity	NPD6416	Phase 2
0.6257	Remote Similarity	NPD3625	Discontinued
0.625	Remote Similarity	NPD7613	Discontinued
0.625	Remote Similarity	NPD6457	Approved
0.6243	Remote Similarity	NPD5918	Discontinued
0.6243	Remote Similarity	NPD5263	Approved
0.6242	Remote Similarity	NPD1344	Phase 2
0.6229	Remote Similarity	NPD2949	Approved
0.6229	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD2950	Approved
0.6215	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD8172	Phase 2
0.6215	Remote Similarity	NPD8173	Phase 2
0.6215	Remote Similarity	NPD5725	Approved
0.6213	Remote Similarity	NPD4178	Approved
0.6213	Remote Similarity	NPD4176	Approved
0.6209	Remote Similarity	NPD5933	Phase 3
0.6209	Remote Similarity	NPD5931	Phase 3
0.6209	Remote Similarity	NPD5932	Phase 3
0.6209	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5060	Phase 1
0.6205	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD8417	Discontinued
0.6203	Remote Similarity	NPD7072	Phase 2
0.6202	Remote Similarity	NPD6519	Phase 2
0.6201	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5823	Approved
0.6196	Remote Similarity	NPD979	Approved
0.6195	Remote Similarity	NPD7791	Approved
0.6195	Remote Similarity	NPD7944	Discontinued
0.6195	Remote Similarity	NPD7952	Approved
0.6195	Remote Similarity	NPD7951	Approved
0.6195	Remote Similarity	NPD7789	Approved
0.6195	Remote Similarity	NPD7790	Approved
0.6195	Remote Similarity	NPD7950	Approved
0.6195	Remote Similarity	NPD7953	Approved
0.619	Remote Similarity	NPD7205	Discontinued
0.6188	Remote Similarity	NPD7730	Approved
0.6188	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7731	Approved
0.6172	Remote Similarity	NPD6321	Discontinued
0.6171	Remote Similarity	NPD4621	Approved
0.6171	Remote Similarity	NPD4619	Approved
0.6171	Remote Similarity	NPD7271	Approved
0.617	Remote Similarity	NPD951	Approved
0.6158	Remote Similarity	NPD2791	Discontinued
0.6158	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD2331	Discontinued
0.6154	Remote Similarity	NPD7854	Phase 2
0.615	Remote Similarity	NPD5086	Approved
0.6141	Remote Similarity	NPD1801	Approved
0.6141	Remote Similarity	NPD1802	Approved
0.6139	Remote Similarity	NPD6891	Phase 2
0.6138	Remote Similarity	NPD7011	Discontinued
0.6136	Remote Similarity	NPD1527	Phase 2
0.6136	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7001	Phase 3
0.6132	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5982	Phase 2
0.6127	Remote Similarity	NPD8240	Discontinued
0.6127	Remote Similarity	NPD2146	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5994	Discontinued
0.6124	Remote Similarity	NPD4601	Approved
0.6124	Remote Similarity	NPD4600	Approved
0.6122	Remote Similarity	NPD3422	Phase 3
0.6122	Remote Similarity	NPD3423	Phase 2
0.612	Remote Similarity	NPD8323	Discontinued
0.6114	Remote Similarity	NPD6489	Phase 3
0.6109	Remote Similarity	NPD7805	Phase 3
0.6108	Remote Similarity	NPD7234	Approved
0.6108	Remote Similarity	NPD7233	Approved
0.6105	Remote Similarity	NPD4393	Approved
0.6105	Remote Similarity	NPD33	Approved
0.6102	Remote Similarity	NPD6623	Phase 3
0.6102	Remote Similarity	NPD5296	Approved
0.6099	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3399	Approved
0.6092	Remote Similarity	NPD5759	Approved
0.6092	Remote Similarity	NPD3626	Phase 3
0.6091	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2670	Approved
0.6085	Remote Similarity	NPD6571	Approved
0.6085	Remote Similarity	NPD6570	Approved
0.6082	Remote Similarity	NPD7581	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7580	Phase 3
0.6081	Remote Similarity	NPD6995	Phase 1
0.608	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5113	Approved
0.6078	Remote Similarity	NPD5112	Approved
0.6078	Remote Similarity	NPD5114	Approved
0.6077	Remote Similarity	NPD4152	Approved
0.6075	Remote Similarity	NPD5748	Phase 2
0.6075	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2994	Approved
0.607	Remote Similarity	NPD7483	Phase 2
0.607	Remote Similarity	NPD7482	Phase 2
0.6066	Remote Similarity	NPD2387	Approved
0.6063	Remote Similarity	NPD3437	Discontinued
0.6062	Remote Similarity	NPD5430	Discontinued
0.6062	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5179	Approved
0.6061	Remote Similarity	NPD5181	Approved
0.6061	Remote Similarity	NPD5180	Approved
0.6058	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3828	Approved
0.6057	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD2613	Approved
0.6056	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7820	Phase 3
0.6054	Remote Similarity	NPD3950	Discontinued
0.6054	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5504	Discontinued

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