NPASS Compound

Structure

CID145754 OpenBabel06191715502D 26 31 0 0 1 0 0 0 0 0999 V2000 0.0477 -0.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0850 3.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 3.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1766 -0.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9958 2.5274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9662 -0.9569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4360 2.7744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1766 0.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8531 1.6268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 -0.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3818 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7849 2.5914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7086 0.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4625 3.2015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2934 1.8739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9662 0.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0019 1.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 0.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7647 0.4966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0625 1.8538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5287 1.3773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1558 1.7585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6752 0.4489 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4334 1.0209 0.0000 N 0 0 0 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 -5.2521 2.7456 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 21 1 1 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 6 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 11 1 6 0 0 0 21 22 1 0 0 0 0 22 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.22
Volume:	365.898
LogP:	2.498
LogD:	2.607
LogS:	-4.338
# Rotatable Bonds:	1
TPSA:	30.54
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	4.22
Fsp3:	0.455
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:	-5.263
MDCK Permeability:	1.019104638544377e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.309
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	73.7411117553711%
Volume Distribution (VD):	3.445
Pgp-substrate:	36.20583724975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.968
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.963
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	7.444
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.234
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.615
Rat Oral Acute Toxicity:	0.468
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.89
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC145754

Natural Product ID:	NPC145754
*Common Name:**	Chimonanthine
IUPAC Name:	(3aR,8bR)-8b-[(3aR,8bR)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole
Synonyms:	Chimonanthine
Standard InCHIKey:	HOYXPMHLHJOGHD-CZYKHXBRSA-N
Standard InCHI:	InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21+,22+/m1/s1
SMILES:	CN1CC[C@@]2(c3ccccc3N[C@H]12)[C@@]12CCN(C)[C@H]2Nc2ccccc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464977
PubChem CID:	442058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO13462	Plocamium costatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075796]
NPO40170	Idiospermum australiense	Species	Calycanthaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[7595588]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16162	Cyclamen cyprium	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15298	Epilachna borealis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14328	Aconitum ouvrardianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12017	Juniperus mexicana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13462	Plocamium costatum	Species	Plocamiaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	58.3	%	PMID[573685]

☑ 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 NPC145754 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	793
0.1-0.2	5936
0.2-0.3	20672
0.3-0.4	9499
0.4-0.5	4098
0.5-0.6	1354
0.6-0.7	315
0.7-0.8	23
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8231	Intermediate Similarity	NPC252794
0.8151	Intermediate Similarity	NPC276085
0.7847	Intermediate Similarity	NPC109787
0.771	Intermediate Similarity	NPC475915
0.7677	Intermediate Similarity	NPC242269
0.76	Intermediate Similarity	NPC222029
0.75	Intermediate Similarity	NPC206592
0.7447	Intermediate Similarity	NPC471123
0.7328	Intermediate Similarity	NPC313673
0.7324	Intermediate Similarity	NPC267508
0.7256	Intermediate Similarity	NPC307396
0.723	Intermediate Similarity	NPC469735
0.7181	Intermediate Similarity	NPC469740
0.7177	Intermediate Similarity	NPC291610
0.7143	Intermediate Similarity	NPC313449
0.7114	Intermediate Similarity	NPC264589
0.709	Intermediate Similarity	NPC264580
0.7086	Intermediate Similarity	NPC318086
0.7083	Intermediate Similarity	NPC128582
0.7081	Intermediate Similarity	NPC475097
0.7051	Intermediate Similarity	NPC68650
0.7032	Intermediate Similarity	NPC469428
0.7031	Intermediate Similarity	NPC79618
0.6986	Remote Similarity	NPC469560
0.6977	Remote Similarity	NPC302790
0.6974	Remote Similarity	NPC473329
0.697	Remote Similarity	NPC187036
0.6941	Remote Similarity	NPC276430
0.6939	Remote Similarity	NPC130251
0.6928	Remote Similarity	NPC66936
0.6899	Remote Similarity	NPC469741
0.6892	Remote Similarity	NPC301760
0.6889	Remote Similarity	NPC192209
0.6866	Remote Similarity	NPC288232
0.6846	Remote Similarity	NPC2949
0.6842	Remote Similarity	NPC314141
0.6813	Remote Similarity	NPC475420
0.6795	Remote Similarity	NPC476297
0.6795	Remote Similarity	NPC476219
0.6769	Remote Similarity	NPC434
0.6755	Remote Similarity	NPC311330
0.6728	Remote Similarity	NPC63047
0.6728	Remote Similarity	NPC475248
0.6726	Remote Similarity	NPC256288
0.6716	Remote Similarity	NPC296163
0.6713	Remote Similarity	NPC209389
0.671	Remote Similarity	NPC475763
0.671	Remote Similarity	NPC53947
0.6709	Remote Similarity	NPC216643
0.6707	Remote Similarity	NPC285622
0.6686	Remote Similarity	NPC2933
0.6667	Remote Similarity	NPC186284
0.6667	Remote Similarity	NPC204141
0.6667	Remote Similarity	NPC474880
0.6667	Remote Similarity	NPC475990
0.6667	Remote Similarity	NPC221786
0.6667	Remote Similarity	NPC22082
0.6647	Remote Similarity	NPC259626
0.6643	Remote Similarity	NPC478079
0.6639	Remote Similarity	NPC191444
0.6623	Remote Similarity	NPC288838
0.6623	Remote Similarity	NPC59084
0.6622	Remote Similarity	NPC198988
0.6612	Remote Similarity	NPC30445
0.6611	Remote Similarity	NPC477179
0.6608	Remote Similarity	NPC473615
0.6606	Remote Similarity	NPC473880
0.6606	Remote Similarity	NPC473743
0.6603	Remote Similarity	NPC33421
0.6591	Remote Similarity	NPC164802
0.6579	Remote Similarity	NPC473868
0.6579	Remote Similarity	NPC469537
0.6579	Remote Similarity	NPC63157
0.6577	Remote Similarity	NPC325252
0.6575	Remote Similarity	NPC477178
0.6575	Remote Similarity	NPC476689
0.6575	Remote Similarity	NPC477181
0.6575	Remote Similarity	NPC254850
0.6575	Remote Similarity	NPC477180
0.6575	Remote Similarity	NPC22079
0.6575	Remote Similarity	NPC476685
0.6575	Remote Similarity	NPC476687
0.657	Remote Similarity	NPC229484
0.6569	Remote Similarity	NPC125416
0.6562	Remote Similarity	NPC471122
0.656	Remote Similarity	NPC329430
0.6557	Remote Similarity	NPC176858
0.6556	Remote Similarity	NPC73767
0.6555	Remote Similarity	NPC169016
0.6552	Remote Similarity	NPC9856
0.6538	Remote Similarity	NPC477174
0.6538	Remote Similarity	NPC477173
0.6538	Remote Similarity	NPC470490
0.6533	Remote Similarity	NPC125746
0.6532	Remote Similarity	NPC292675
0.6532	Remote Similarity	NPC108800
0.6531	Remote Similarity	NPC475450
0.6528	Remote Similarity	NPC476950
0.6522	Remote Similarity	NPC472102
0.6522	Remote Similarity	NPC229173
0.6522	Remote Similarity	NPC309531
0.6513	Remote Similarity	NPC469780
0.6513	Remote Similarity	NPC469768
0.6513	Remote Similarity	NPC469783
0.6513	Remote Similarity	NPC469761
0.6513	Remote Similarity	NPC469767
0.6513	Remote Similarity	NPC469784
0.6513	Remote Similarity	NPC469779
0.6509	Remote Similarity	NPC314919
0.6503	Remote Similarity	NPC470488
0.65	Remote Similarity	NPC229477
0.65	Remote Similarity	NPC61013
0.65	Remote Similarity	NPC123241
0.6481	Remote Similarity	NPC99632
0.6481	Remote Similarity	NPC282339
0.6471	Remote Similarity	NPC134825
0.6471	Remote Similarity	NPC469766
0.6467	Remote Similarity	NPC470491
0.6467	Remote Similarity	NPC475259
0.6467	Remote Similarity	NPC471950
0.6467	Remote Similarity	NPC471945
0.6467	Remote Similarity	NPC218268
0.646	Remote Similarity	NPC193410
0.646	Remote Similarity	NPC36495
0.6447	Remote Similarity	NPC88097
0.6447	Remote Similarity	NPC110126
0.6447	Remote Similarity	NPC104483
0.6446	Remote Similarity	NPC355
0.6433	Remote Similarity	NPC2272
0.6432	Remote Similarity	NPC471951
0.6432	Remote Similarity	NPC471946
0.6429	Remote Similarity	NPC320147
0.6424	Remote Similarity	NPC84911
0.642	Remote Similarity	NPC248117
0.6414	Remote Similarity	NPC250361
0.6412	Remote Similarity	NPC286994
0.641	Remote Similarity	NPC143872
0.6402	Remote Similarity	NPC471124
0.6398	Remote Similarity	NPC191817
0.6398	Remote Similarity	NPC475359
0.6398	Remote Similarity	NPC286427
0.6395	Remote Similarity	NPC473587
0.6386	Remote Similarity	NPC474897
0.638	Remote Similarity	NPC286871
0.638	Remote Similarity	NPC293458
0.6376	Remote Similarity	NPC316104
0.6376	Remote Similarity	NPC162417
0.6369	Remote Similarity	NPC21605
0.6364	Remote Similarity	NPC214960
0.6364	Remote Similarity	NPC279527
0.6358	Remote Similarity	NPC135141
0.6358	Remote Similarity	NPC261195
0.6358	Remote Similarity	NPC29886
0.6358	Remote Similarity	NPC92796
0.6358	Remote Similarity	NPC96102
0.6358	Remote Similarity	NPC41257
0.6351	Remote Similarity	NPC475428
0.6341	Remote Similarity	NPC111233
0.6336	Remote Similarity	NPC474430
0.6329	Remote Similarity	NPC37548
0.6327	Remote Similarity	NPC473762
0.6323	Remote Similarity	NPC20144
0.6323	Remote Similarity	NPC472103
0.632	Remote Similarity	NPC470926
0.6316	Remote Similarity	NPC16659
0.6316	Remote Similarity	NPC105127
0.6312	Remote Similarity	NPC226143
0.6309	Remote Similarity	NPC179365
0.6301	Remote Similarity	NPC472294
0.6299	Remote Similarity	NPC115611
0.6289	Remote Similarity	NPC243756
0.6289	Remote Similarity	NPC154602
0.6284	Remote Similarity	NPC471436
0.6282	Remote Similarity	NPC242556
0.628	Remote Similarity	NPC315498
0.628	Remote Similarity	NPC470203
0.628	Remote Similarity	NPC230942
0.6279	Remote Similarity	NPC317642
0.6275	Remote Similarity	NPC315051
0.6268	Remote Similarity	NPC279385
0.6268	Remote Similarity	NPC179605
0.6267	Remote Similarity	NPC473930
0.6266	Remote Similarity	NPC477134
0.6264	Remote Similarity	NPC476095
0.626	Remote Similarity	NPC262295
0.6258	Remote Similarity	NPC318065
0.6258	Remote Similarity	NPC56765
0.6258	Remote Similarity	NPC206819
0.6257	Remote Similarity	NPC265710
0.625	Remote Similarity	NPC122106
0.625	Remote Similarity	NPC285381
0.625	Remote Similarity	NPC85482
0.625	Remote Similarity	NPC117032
0.625	Remote Similarity	NPC41174
0.6242	Remote Similarity	NPC470440
0.6242	Remote Similarity	NPC314372
0.6235	Remote Similarity	NPC225857
0.6228	Remote Similarity	NPC167724
0.6228	Remote Similarity	NPC224970
0.6228	Remote Similarity	NPC223595

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 NPC145754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	656
0.2-0.3	1265
0.3-0.4	1891
0.4-0.5	3298
0.5-0.6	1455
0.6-0.7	250
0.7-0.8	24
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
0.7955	Intermediate Similarity	NPD1950	Approved
0.7955	Intermediate Similarity	NPD1949	Approved
0.7903	Intermediate Similarity	NPD2999	Approved
0.7903	Intermediate Similarity	NPD3001	Approved
0.7742	Intermediate Similarity	NPD4116	Approved
0.7594	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3545	Approved
0.75	Intermediate Similarity	NPD3546	Approved
0.7481	Intermediate Similarity	NPD2143	Discontinued
0.744	Intermediate Similarity	NPD4115	Approved
0.744	Intermediate Similarity	NPD4114	Approved
0.7391	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2038	Approved
0.7344	Intermediate Similarity	NPD2039	Approved
0.7323	Intermediate Similarity	NPD7633	Discontinued
0.7302	Intermediate Similarity	NPD5253	Approved
0.7299	Intermediate Similarity	NPD6900	Discontinued
0.7244	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2914	Approved
0.7231	Intermediate Similarity	NPD2913	Approved
0.7197	Intermediate Similarity	NPD2463	Approved
0.7197	Intermediate Similarity	NPD2467	Approved
0.7197	Intermediate Similarity	NPD2464	Approved
0.7177	Intermediate Similarity	NPD4734	Approved
0.7177	Intermediate Similarity	NPD4735	Approved
0.7153	Intermediate Similarity	NPD2940	Approved
0.7153	Intermediate Similarity	NPD2938	Approved
0.7143	Intermediate Similarity	NPD7481	Approved
0.7143	Intermediate Similarity	NPD8263	Discontinued
0.7143	Intermediate Similarity	NPD7480	Approved
0.7121	Intermediate Similarity	NPD1720	Phase 2
0.7121	Intermediate Similarity	NPD1723	Phase 2
0.7105	Intermediate Similarity	NPD8400	Approved
0.7105	Intermediate Similarity	NPD8402	Approved
0.7105	Intermediate Similarity	NPD8401	Approved
0.705	Intermediate Similarity	NPD3240	Phase 2
0.6978	Remote Similarity	NPD8128	Discontinued
0.6972	Remote Similarity	NPD4867	Approved
0.6972	Remote Similarity	NPD3841	Phase 3
0.6972	Remote Similarity	NPD4866	Approved
0.6941	Remote Similarity	NPD8240	Discontinued
0.6929	Remote Similarity	NPD2840	Approved
0.6923	Remote Similarity	NPD8630	Approved
0.6899	Remote Similarity	NPD6300	Approved
0.6899	Remote Similarity	NPD6299	Approved
0.6861	Remote Similarity	NPD6892	Discontinued
0.6822	Remote Similarity	NPD993	Approved
0.6822	Remote Similarity	NPD990	Approved
0.6815	Remote Similarity	NPD6070	Approved
0.6815	Remote Similarity	NPD6069	Approved
0.6794	Remote Similarity	NPD3548	Approved
0.6791	Remote Similarity	NPD1813	Discontinued
0.6791	Remote Similarity	NPD5629	Discontinued
0.6788	Remote Similarity	NPD3499	Approved
0.6788	Remote Similarity	NPD3498	Approved
0.6783	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4543	Discontinued
0.6716	Remote Similarity	NPD5179	Approved
0.6716	Remote Similarity	NPD5181	Approved
0.6716	Remote Similarity	NPD5180	Approved
0.671	Remote Similarity	NPD2172	Phase 1
0.6694	Remote Similarity	NPD5554	Approved
0.6691	Remote Similarity	NPD6660	Discontinued
0.6667	Remote Similarity	NPD3625	Discontinued
0.6667	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1539	Approved
0.6646	Remote Similarity	NPD2150	Discontinued
0.664	Remote Similarity	NPD2005	Discontinued
0.6622	Remote Similarity	NPD1515	Discontinued
0.6601	Remote Similarity	NPD5254	Discontinued
0.6597	Remote Similarity	NPD3011	Approved
0.6597	Remote Similarity	NPD3008	Approved
0.6597	Remote Similarity	NPD3012	Approved
0.6591	Remote Similarity	NPD477	Phase 1
0.6584	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5244	Approved
0.6569	Remote Similarity	NPD5243	Approved
0.6569	Remote Similarity	NPD5245	Approved
0.6565	Remote Similarity	NPD1064	Approved
0.6565	Remote Similarity	NPD1065	Approved
0.6554	Remote Similarity	NPD3385	Approved
0.6547	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5631	Phase 3
0.6541	Remote Similarity	NPD1108	Approved
0.6541	Remote Similarity	NPD1107	Approved
0.6524	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3983	Phase 3
0.6516	Remote Similarity	NPD1683	Approved
0.6507	Remote Similarity	NPD3654	Approved
0.6503	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2340	Discontinued
0.6496	Remote Similarity	NPD2622	Approved
0.6494	Remote Similarity	NPD5060	Phase 1
0.6486	Remote Similarity	NPD7200	Approved
0.6479	Remote Similarity	NPD2964	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7072	Phase 2
0.6475	Remote Similarity	NPD5657	Phase 3
0.6471	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5526	Phase 2
0.6471	Remote Similarity	NPD6301	Phase 2
0.6467	Remote Similarity	NPD6358	Phase 2
0.6467	Remote Similarity	NPD6342	Discontinued
0.6452	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD786	Approved
0.6433	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3100	Discontinued
0.6429	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5178	Approved
0.6417	Remote Similarity	NPD2539	Approved
0.6417	Remote Similarity	NPD2538	Approved
0.6412	Remote Similarity	NPD1728	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD153	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD560	Approved
0.6397	Remote Similarity	NPD561	Approved
0.6393	Remote Similarity	NPD4146	Approved
0.6393	Remote Similarity	NPD4145	Approved
0.6392	Remote Similarity	NPD4462	Approved
0.6392	Remote Similarity	NPD4463	Approved
0.6391	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1937	Approved
0.6382	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD202	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5915	Approved
0.637	Remote Similarity	NPD2036	Approved
0.6364	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1722	Approved
0.6358	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4411	Phase 1
0.6357	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5063	Approved
0.635	Remote Similarity	NPD5064	Approved
0.6335	Remote Similarity	NPD2927	Phase 3
0.632	Remote Similarity	NPD2998	Approved
0.632	Remote Similarity	NPD3000	Approved
0.632	Remote Similarity	NPD2997	Approved
0.6319	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1262	Discovery
0.6316	Remote Similarity	NPD2528	Approved
0.6312	Remote Similarity	NPD5516	Phase 2
0.6312	Remote Similarity	NPD2790	Discontinued
0.6312	Remote Similarity	NPD5517	Phase 2
0.6309	Remote Similarity	NPD1316	Discontinued
0.6303	Remote Similarity	NPD4796	Discontinued
0.6299	Remote Similarity	NPD6768	Approved
0.6294	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5600	Discontinued
0.6291	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2399	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2867	Approved
0.629	Remote Similarity	NPD771	Phase 3
0.6289	Remote Similarity	NPD8355	Approved
0.6289	Remote Similarity	NPD8353	Approved
0.6288	Remote Similarity	NPD4937	Approved
0.6288	Remote Similarity	NPD4936	Approved
0.6286	Remote Similarity	NPD299	Phase 3
0.6284	Remote Similarity	NPD6489	Phase 3
0.628	Remote Similarity	NPD1743	Approved
0.628	Remote Similarity	NPD1742	Approved
0.628	Remote Similarity	NPD19	Approved
0.6259	Remote Similarity	NPD2925	Approved
0.6259	Remote Similarity	NPD2924	Approved
0.625	Remote Similarity	NPD5318	Discontinued
0.625	Remote Similarity	NPD6828	Phase 2
0.625	Remote Similarity	NPD5963	Phase 2
0.625	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3248	Phase 1
0.625	Remote Similarity	NPD5964	Phase 2
0.6235	Remote Similarity	NPD7091	Discontinued
0.6233	Remote Similarity	NPD572	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6561	Approved
0.6232	Remote Similarity	NPD6562	Approved
0.6226	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5962	Phase 2
0.622	Remote Similarity	NPD5989	Phase 1
0.622	Remote Similarity	NPD4542	Approved
0.622	Remote Similarity	NPD4545	Approved
0.6218	Remote Similarity	NPD2866	Approved
0.6216	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8354	Approved
0.621	Remote Similarity	NPD5675	Discontinued
0.6205	Remote Similarity	NPD1313	Approved
0.6205	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD526	Approved
0.6203	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5597	Approved
0.6202	Remote Similarity	NPD5598	Approved
0.6196	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7160	Approved
0.619	Remote Similarity	NPD5436	Phase 1
0.6187	Remote Similarity	NPD7062	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