NPASS Compound

Structure

NPC470483 OpenBabel07101718232D 25 30 0 0 1 0 0 0 0 0999 V2000 -0.9429 -4.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6576 -0.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8871 -0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0628 -1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 -1.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0307 -1.6597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0785 -2.7054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6657 -3.5349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5218 -1.3197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6975 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7154 -2.2711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9270 -1.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7730 -1.5024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4286 -2.5634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6256 -3.8154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2232 -2.8031 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 12 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 15 1 0 0 0 0 4 16 2 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 12 23 2 0 0 0 0 13 5 1 6 0 0 0 13 14 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 6 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 6 0 0 0 20 21 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.16
Volume:	338.319
LogP:	2.414
LogD:	1.84
LogS:	-3.881
# Rotatable Bonds:	1
TPSA:	53.01
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	6.143
Fsp3:	0.55
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:	-4.762
MDCK Permeability:	1.8065946278511547e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.526

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	40.54316329956055%
Volume Distribution (VD):	1.257
Pgp-substrate:	63.677894592285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.53
CYP2C9-substrate:	0.186
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.94

ADMET: Excretion

Clearance (CL):	6.562
Half-life (T1/2):	0.678

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.357
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC470483

Natural Product ID:	NPC470483
*Common Name:**	Geissospermidine
IUPAC Name:	n.a.
Synonyms:	Geissospermidine
Standard InCHIKey:	FPEWLKWWYJYGBX-IQCLKLAJSA-N
Standard InCHI:	InChI=1S/C20H22N2O3/c1-12(23)22-17-11-13-5-8-21-9-7-19(17,20(21)14(13)6-10-25-20)15-3-2-4-16(24)18(15)22/h2-4,6,13,17,24H,5,7-11H2,1H3/t13-,17+,19-,20+/m1/s1
SMILES:	CC(=O)N1C2CC3CCN4CCC2(C45C3=CCO5)C6=C1C(=CC=C6)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047337
PubChem CID:	70686216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO32721	geissospermum reticulatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22551062]

☑ 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
GI50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1021	Organism	Leishmania infantum	Leishmania infantum	GI50	>	100.0	ug.mL-1	PMID[530158]

☑ 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 NPC470483 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	320
0.1-0.2	1410
0.2-0.3	5411
0.3-0.4	11941
0.4-0.5	16381
0.5-0.6	6056
0.6-0.7	1105
0.7-0.8	68
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9883	High Similarity	NPC470485
0.9231	High Similarity	NPC470484
0.8772	High Similarity	NPC33507
0.8245	Intermediate Similarity	NPC161804
0.8031	Intermediate Similarity	NPC1464
0.7835	Intermediate Similarity	NPC127178
0.7737	Intermediate Similarity	NPC22689
0.7737	Intermediate Similarity	NPC105055
0.7732	Intermediate Similarity	NPC138615
0.7732	Intermediate Similarity	NPC132874
0.7732	Intermediate Similarity	NPC265642
0.7732	Intermediate Similarity	NPC218733
0.7653	Intermediate Similarity	NPC138830
0.7638	Intermediate Similarity	NPC195787
0.7638	Intermediate Similarity	NPC246140
0.7608	Intermediate Similarity	NPC477394
0.7585	Intermediate Similarity	NPC10653
0.7585	Intermediate Similarity	NPC318525
0.7536	Intermediate Similarity	NPC471513
0.7476	Intermediate Similarity	NPC234772
0.7475	Intermediate Similarity	NPC67904
0.746	Intermediate Similarity	NPC116096
0.7432	Intermediate Similarity	NPC70172
0.7409	Intermediate Similarity	NPC217294
0.7383	Intermediate Similarity	NPC477397
0.7371	Intermediate Similarity	NPC473458
0.7368	Intermediate Similarity	NPC222046
0.7368	Intermediate Similarity	NPC288110
0.7364	Intermediate Similarity	NPC477395
0.735	Intermediate Similarity	NPC469732
0.733	Intermediate Similarity	NPC470481
0.733	Intermediate Similarity	NPC470482
0.733	Intermediate Similarity	NPC98197
0.7322	Intermediate Similarity	NPC472101
0.7322	Intermediate Similarity	NPC472120
0.7316	Intermediate Similarity	NPC166169
0.7282	Intermediate Similarity	NPC5630
0.7246	Intermediate Similarity	NPC159815
0.7228	Intermediate Similarity	NPC472117
0.7202	Intermediate Similarity	NPC302235
0.7172	Intermediate Similarity	NPC78284
0.7157	Intermediate Similarity	NPC203628
0.7151	Intermediate Similarity	NPC472106
0.7143	Intermediate Similarity	NPC477393
0.7143	Intermediate Similarity	NPC139085
0.7143	Intermediate Similarity	NPC214626
0.7143	Intermediate Similarity	NPC251212
0.713	Intermediate Similarity	NPC470480
0.7123	Intermediate Similarity	NPC475609
0.7123	Intermediate Similarity	NPC219397
0.7121	Intermediate Similarity	NPC473004
0.7121	Intermediate Similarity	NPC204970
0.7117	Intermediate Similarity	NPC469450
0.7114	Intermediate Similarity	NPC100863
0.7101	Intermediate Similarity	NPC477160
0.71	Intermediate Similarity	NPC303214
0.7081	Intermediate Similarity	NPC127996
0.708	Intermediate Similarity	NPC477396
0.7075	Intermediate Similarity	NPC77777
0.7065	Intermediate Similarity	NPC469428
0.7054	Intermediate Similarity	NPC469452
0.7054	Intermediate Similarity	NPC469451
0.7047	Intermediate Similarity	NPC39822
0.7045	Intermediate Similarity	NPC186284
0.7045	Intermediate Similarity	NPC22082
0.7043	Intermediate Similarity	NPC85651
0.7037	Intermediate Similarity	NPC231924
0.7027	Intermediate Similarity	NPC131977
0.701	Intermediate Similarity	NPC232600
0.6996	Remote Similarity	NPC301501
0.6991	Remote Similarity	NPC329932
0.699	Remote Similarity	NPC473007
0.6989	Remote Similarity	NPC309531
0.6989	Remote Similarity	NPC472102
0.6986	Remote Similarity	NPC223242
0.6982	Remote Similarity	NPC291173
0.698	Remote Similarity	NPC272706
0.6977	Remote Similarity	NPC128476
0.6976	Remote Similarity	NPC52801
0.6973	Remote Similarity	NPC113946
0.6965	Remote Similarity	NPC243626
0.6959	Remote Similarity	NPC19175
0.6947	Remote Similarity	NPC469915
0.6944	Remote Similarity	NPC250960
0.6944	Remote Similarity	NPC472100
0.6944	Remote Similarity	NPC251071
0.6944	Remote Similarity	NPC264589
0.6944	Remote Similarity	NPC71539
0.6935	Remote Similarity	NPC174629
0.6927	Remote Similarity	NPC266994
0.6923	Remote Similarity	NPC139373
0.6919	Remote Similarity	NPC21425
0.6908	Remote Similarity	NPC87714
0.6891	Remote Similarity	NPC129624
0.6881	Remote Similarity	NPC230313
0.6875	Remote Similarity	NPC473743
0.6872	Remote Similarity	NPC474470
0.6869	Remote Similarity	NPC126556
0.6869	Remote Similarity	NPC262725
0.6864	Remote Similarity	NPC74216
0.6862	Remote Similarity	NPC315498
0.6862	Remote Similarity	NPC230942
0.6856	Remote Similarity	NPC477187
0.6856	Remote Similarity	NPC260075
0.685	Remote Similarity	NPC474059
0.685	Remote Similarity	NPC473008
0.685	Remote Similarity	NPC473569
0.685	Remote Similarity	NPC473298
0.6845	Remote Similarity	NPC471512
0.6845	Remote Similarity	NPC471122
0.684	Remote Similarity	NPC10732
0.6834	Remote Similarity	NPC181928
0.6825	Remote Similarity	NPC269449
0.6825	Remote Similarity	NPC313757
0.6821	Remote Similarity	NPC321211
0.6821	Remote Similarity	NPC218594
0.6821	Remote Similarity	NPC99043
0.6818	Remote Similarity	NPC322621
0.6818	Remote Similarity	NPC476095
0.6816	Remote Similarity	NPC25401
0.6814	Remote Similarity	NPC472191
0.6814	Remote Similarity	NPC90967
0.6812	Remote Similarity	NPC473005
0.6808	Remote Similarity	NPC473006
0.6804	Remote Similarity	NPC225597
0.6804	Remote Similarity	NPC470739
0.6804	Remote Similarity	NPC477640
0.6802	Remote Similarity	NPC159963
0.68	Remote Similarity	NPC477186
0.6798	Remote Similarity	NPC221687
0.6796	Remote Similarity	NPC475489
0.6791	Remote Similarity	NPC195636
0.6789	Remote Similarity	NPC471124
0.6788	Remote Similarity	NPC266176
0.6788	Remote Similarity	NPC475686
0.6788	Remote Similarity	NPC290759
0.6788	Remote Similarity	NPC82533
0.6788	Remote Similarity	NPC477185
0.6788	Remote Similarity	NPC158148
0.6788	Remote Similarity	NPC58766
0.6777	Remote Similarity	NPC168250
0.6776	Remote Similarity	NPC189661
0.6766	Remote Similarity	NPC474904
0.6765	Remote Similarity	NPC162653
0.6762	Remote Similarity	NPC212123
0.6761	Remote Similarity	NPC119722
0.6755	Remote Similarity	NPC301163
0.6753	Remote Similarity	NPC311991
0.6753	Remote Similarity	NPC474475
0.6751	Remote Similarity	NPC118633
0.6751	Remote Similarity	NPC294790
0.6751	Remote Similarity	NPC148693
0.675	Remote Similarity	NPC285841
0.6749	Remote Similarity	NPC302001
0.6746	Remote Similarity	NPC14339
0.6738	Remote Similarity	NPC29285
0.6737	Remote Similarity	NPC249274
0.6736	Remote Similarity	NPC85482
0.6735	Remote Similarity	NPC287152
0.6733	Remote Similarity	NPC22476
0.6721	Remote Similarity	NPC212799
0.672	Remote Similarity	NPC225319
0.6718	Remote Similarity	NPC264482
0.6718	Remote Similarity	NPC203202
0.6717	Remote Similarity	NPC99179
0.6717	Remote Similarity	NPC220961
0.6716	Remote Similarity	NPC320088
0.6714	Remote Similarity	NPC474145
0.6714	Remote Similarity	NPC475841
0.6712	Remote Similarity	NPC148124
0.6711	Remote Similarity	NPC476220
0.6711	Remote Similarity	NPC160113
0.6703	Remote Similarity	NPC475763
0.6701	Remote Similarity	NPC181138
0.6701	Remote Similarity	NPC293255
0.6701	Remote Similarity	NPC298851
0.6701	Remote Similarity	NPC21752
0.6701	Remote Similarity	NPC473880
0.6701	Remote Similarity	NPC210415
0.6701	Remote Similarity	NPC70092
0.6701	Remote Similarity	NPC237044
0.6701	Remote Similarity	NPC276993
0.6701	Remote Similarity	NPC96901
0.67	Remote Similarity	NPC33902
0.67	Remote Similarity	NPC276674
0.6699	Remote Similarity	NPC17677
0.6697	Remote Similarity	NPC476069
0.6683	Remote Similarity	NPC471489
0.6683	Remote Similarity	NPC170333
0.6683	Remote Similarity	NPC473375
0.6683	Remote Similarity	NPC237579
0.6683	Remote Similarity	NPC97100
0.6682	Remote Similarity	NPC470821
0.6682	Remote Similarity	NPC478075
0.6681	Remote Similarity	NPC154922
0.6667	Remote Similarity	NPC46259
0.6667	Remote Similarity	NPC15919
0.6667	Remote Similarity	NPC214960
0.6667	Remote Similarity	NPC279527
0.6667	Remote Similarity	NPC270301

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 NPC470483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	577
0.2-0.3	681
0.3-0.4	1672
0.4-0.5	3133
0.5-0.6	2535
0.6-0.7	350
0.7-0.8	3
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
0.7302	Intermediate Similarity	NPD5600	Discontinued
0.7273	Intermediate Similarity	NPD5582	Discontinued
0.7188	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3983	Phase 3
0.6944	Remote Similarity	NPD3141	Discontinued
0.6878	Remote Similarity	NPD4796	Discontinued
0.6862	Remote Similarity	NPD19	Approved
0.6862	Remote Similarity	NPD1742	Approved
0.6862	Remote Similarity	NPD1743	Approved
0.6859	Remote Similarity	NPD5847	Phase 1
0.6845	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7479	Phase 2
0.6791	Remote Similarity	NPD1769	Discontinued
0.6766	Remote Similarity	NPD7628	Phase 3
0.6766	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7630	Phase 3
0.6763	Remote Similarity	NPD6321	Discontinued
0.6754	Remote Similarity	NPD6037	Discontinued
0.6753	Remote Similarity	NPD5938	Phase 3
0.6742	Remote Similarity	NPD1753	Discontinued
0.6738	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4120	Approved
0.672	Remote Similarity	NPD4121	Phase 3
0.6684	Remote Similarity	NPD5743	Approved
0.6684	Remote Similarity	NPD5742	Approved
0.6684	Remote Similarity	NPD5741	Approved
0.6684	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3793	Phase 3
0.6682	Remote Similarity	NPD7263	Phase 2
0.6667	Remote Similarity	NPD4726	Approved
0.6667	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD4725	Approved
0.6649	Remote Similarity	NPD2970	Approved
0.6649	Remote Similarity	NPD2969	Approved
0.6649	Remote Similarity	NPD3975	Discontinued
0.6636	Remote Similarity	NPD6997	Phase 2
0.6634	Remote Similarity	NPD3398	Discontinued
0.6633	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3437	Discontinued
0.6616	Remote Similarity	NPD6878	Phase 2
0.6616	Remote Similarity	NPD6879	Phase 2
0.6615	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2489	Approved
0.6615	Remote Similarity	NPD27	Approved
0.6606	Remote Similarity	NPD7820	Phase 3
0.66	Remote Similarity	NPD4577	Approved
0.66	Remote Similarity	NPD4578	Approved
0.6599	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3051	Approved
0.6593	Remote Similarity	NPD4430	Phase 2
0.659	Remote Similarity	NPD7047	Phase 3
0.6582	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.658	Remote Similarity	NPD5823	Approved
0.6579	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6283	Phase 2
0.6578	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7906	Approved
0.6548	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3557	Approved
0.6545	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3558	Approved
0.6545	Remote Similarity	NPD3560	Approved
0.6545	Remote Similarity	NPD3556	Approved
0.6543	Remote Similarity	NPD6357	Discontinued
0.6532	Remote Similarity	NPD3912	Discontinued
0.6526	Remote Similarity	NPD7222	Phase 2
0.6524	Remote Similarity	NPD6238	Discontinued
0.6522	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8016	Phase 3
0.652	Remote Similarity	NPD2845	Phase 2
0.652	Remote Similarity	NPD2843	Phase 2
0.6517	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3636	Approved
0.6514	Remote Similarity	NPD3637	Approved
0.6514	Remote Similarity	NPD3635	Approved
0.6513	Remote Similarity	NPD6071	Discontinued
0.6509	Remote Similarity	NPD6644	Discontinued
0.6508	Remote Similarity	NPD5617	Suspended
0.6507	Remote Similarity	NPD2175	Phase 3
0.6507	Remote Similarity	NPD2176	Approved
0.6507	Remote Similarity	NPD2177	Approved
0.6505	Remote Similarity	NPD7262	Phase 1
0.6502	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD4663	Approved
0.6502	Remote Similarity	NPD4951	Discontinued
0.6495	Remote Similarity	NPD2916	Discontinued
0.6489	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5164	Discontinued
0.6481	Remote Similarity	NPD4502	Phase 2
0.6481	Remote Similarity	NPD5939	Approved
0.6481	Remote Similarity	NPD5936	Approved
0.648	Remote Similarity	NPD2791	Discontinued
0.6471	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4897	Phase 2
0.6467	Remote Similarity	NPD5754	Discontinued
0.6462	Remote Similarity	NPD7126	Discontinued
0.6462	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5858	Discontinued
0.6447	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4481	Phase 3
0.6441	Remote Similarity	NPD5506	Approved
0.6441	Remote Similarity	NPD5507	Approved
0.6432	Remote Similarity	NPD1294	Discontinued
0.6429	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5186	Approved
0.6429	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5183	Approved
0.6425	Remote Similarity	NPD5610	Approved
0.6417	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1945	Phase 1
0.64	Remote Similarity	NPD4103	Phase 2
0.64	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.639	Remote Similarity	NPD8025	Phase 2
0.639	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD3595	Approved
0.6384	Remote Similarity	NPD2606	Approved
0.6384	Remote Similarity	NPD3594	Approved
0.6384	Remote Similarity	NPD2605	Approved
0.6379	Remote Similarity	NPD4659	Approved
0.6378	Remote Similarity	NPD6379	Discontinued
0.6378	Remote Similarity	NPD6457	Approved
0.6372	Remote Similarity	NPD7452	Approved
0.6372	Remote Similarity	NPD6290	Phase 2
0.6372	Remote Similarity	NPD7453	Approved
0.6368	Remote Similarity	NPD3416	Discontinued
0.6368	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7805	Phase 3
0.6368	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2421	Approved
0.6364	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2420	Approved
0.6359	Remote Similarity	NPD4257	Approved
0.6359	Remote Similarity	NPD4256	Phase 2
0.6355	Remote Similarity	NPD7310	Approved
0.6355	Remote Similarity	NPD7311	Approved
0.6355	Remote Similarity	NPD7312	Approved
0.6355	Remote Similarity	NPD7281	Phase 3
0.6355	Remote Similarity	NPD7280	Phase 3
0.6355	Remote Similarity	NPD7313	Approved
0.6355	Remote Similarity	NPD4465	Phase 2
0.6355	Remote Similarity	NPD4467	Phase 2
0.6354	Remote Similarity	NPD7248	Discontinued
0.6351	Remote Similarity	NPD2899	Discontinued
0.635	Remote Similarity	NPD6042	Phase 2
0.635	Remote Similarity	NPD42	Phase 2
0.6348	Remote Similarity	NPD5155	Approved
0.6348	Remote Similarity	NPD5156	Approved
0.6345	Remote Similarity	NPD4166	Phase 2
0.6345	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4515	Suspended
0.6341	Remote Similarity	NPD2383	Phase 1
0.6333	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4604	Approved
0.6333	Remote Similarity	NPD4605	Approved
0.6329	Remote Similarity	NPD2488	Approved
0.6329	Remote Similarity	NPD2490	Approved
0.6327	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8167	Discontinued
0.6324	Remote Similarity	NPD7309	Approved
0.6324	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6636	Phase 3
0.6313	Remote Similarity	NPD4437	Phase 3
0.6313	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7293	Approved
0.6305	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4494	Approved
0.6301	Remote Similarity	NPD4492	Approved
0.6296	Remote Similarity	NPD4596	Phase 1
0.6296	Remote Similarity	NPD6090	Discontinued
0.6293	Remote Similarity	NPD6339	Approved
0.6293	Remote Similarity	NPD6340	Approved
0.6291	Remote Similarity	NPD2494	Approved
0.6291	Remote Similarity	NPD3452	Approved
0.6291	Remote Similarity	NPD3450	Approved
0.6291	Remote Similarity	NPD2493	Approved
0.6289	Remote Similarity	NPD2560	Approved

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