NPASS Compound

Structure

NPC475489 OpenBabel07101718192D 37 44 0 0 1 0 0 0 0 0999 V2000 -5.0395 0.1776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1514 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4176 -0.6559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1313 -0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8383 -2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8601 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1910 -1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8913 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.8364 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 3.3913 0.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8860 0.0412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6086 0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2003 -0.7045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5823 -0.7045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3913 -0.1167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7477 0.5864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 1.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8913 -1.6555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5827 1.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5823 -0.7045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3147 -0.1636 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4487 -0.1636 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.2733 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6086 -0.0681 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 4.2573 1.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3222 -1.9646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9225 0.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -2.2433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 3 31 1 0 0 0 0 4 29 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 2 0 0 0 0 8 21 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 10 23 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 13 36 1 0 0 0 0 14 29 1 0 0 0 0 14 31 1 0 0 0 0 15 2 1 1 0 0 0 15 17 1 0 0 0 0 16 11 1 1 0 0 0 16 24 1 0 0 0 0 16 27 1 0 0 0 0 17 12 1 6 0 0 0 17 24 1 0 0 0 0 18 13 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 30 1 0 0 0 0 20 29 1 6 0 0 0 21 32 1 0 0 0 0 22 9 1 6 0 0 0 22 24 1 0 0 0 0 22 37 1 0 0 0 0 23 30 1 6 0 0 0 23 36 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 27 34 2 0 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 28 32 1 0 0 0 0 28 35 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.26
Volume:	509.11
LogP:	2.121
LogD:	2.775
LogS:	-4.312
# Rotatable Bonds:	4
TPSA:	79.31
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	7.168
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.458
MDCK Permeability:	2.822599526552949e-05
Pgp-inhibitor:	0.703
Pgp-substrate:	0.242
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	45.14936065673828%
Volume Distribution (VD):	1.89
Pgp-substrate:	48.18536376953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	13.437
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.919
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.156
Carcinogencity:	0.287
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC475489

Natural Product ID:	NPC475489
*Common Name:**	Gelsebanine
IUPAC Name:	n.a.
Synonyms:	Gelsebanine
Standard InCHIKey:	QTXUXQFNNPLFTD-SEDTUDQNSA-N
Standard InCHI:	InChI=1S/C30H36N2O5/c1-4-29-14-31(3)25-18-13-36-23(10-20(18)29)30(26(25)29)19-7-5-6-8-21(19)32(28(30)35)11-16-24-17(12-33)15(2)9-22(24)37-27(16)34/h4-8,15-18,20,22-26,33H,1,9-14H2,2-3H3/t15-,16-,17+,18-,20+,22-,23+,24+,25?,26?,29-,30-/m0/s1
SMILES:	CC1CC2C(C1CO)C(C(=O)O2)CN3C4=CC=CC=C4C5(C3=O)C6CC7C(CO6)C8C5C7(CN8C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506584
PubChem CID:	16086585
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003758] Gelsemium 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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	10000.0	nM	PMID[544140]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[544140]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[544140]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[544140]

☑ 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 NPC475489 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	293
0.1-0.2	1335
0.2-0.3	3223
0.3-0.4	13327
0.4-0.5	19741
0.5-0.6	4038
0.6-0.7	653
0.7-0.8	86
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8187	Intermediate Similarity	NPC302548
0.8093	Intermediate Similarity	NPC475559
0.8	Intermediate Similarity	NPC90967
0.7876	Intermediate Similarity	NPC105055
0.7876	Intermediate Similarity	NPC22689
0.7857	Intermediate Similarity	NPC472101
0.7857	Intermediate Similarity	NPC472120
0.7772	Intermediate Similarity	NPC472106
0.7766	Intermediate Similarity	NPC476441
0.775	Intermediate Similarity	NPC471512
0.7716	Intermediate Similarity	NPC34717
0.7692	Intermediate Similarity	NPC473298
0.7685	Intermediate Similarity	NPC475316
0.7685	Intermediate Similarity	NPC473486
0.768	Intermediate Similarity	NPC181928
0.7668	Intermediate Similarity	NPC52262
0.7663	Intermediate Similarity	NPC472117
0.766	Intermediate Similarity	NPC476425
0.764	Intermediate Similarity	NPC212799
0.7639	Intermediate Similarity	NPC470631
0.7639	Intermediate Similarity	NPC35390
0.7639	Intermediate Similarity	NPC473781
0.7609	Intermediate Similarity	NPC309531
0.7609	Intermediate Similarity	NPC472102
0.7538	Intermediate Similarity	NPC221687
0.7514	Intermediate Similarity	NPC201424
0.7513	Intermediate Similarity	NPC476428
0.75	Intermediate Similarity	NPC113946
0.75	Intermediate Similarity	NPC473375
0.75	Intermediate Similarity	NPC97100
0.7446	Intermediate Similarity	NPC29285
0.7441	Intermediate Similarity	NPC234772
0.7419	Intermediate Similarity	NPC315368
0.7419	Intermediate Similarity	NPC225319
0.7382	Intermediate Similarity	NPC96901
0.738	Intermediate Similarity	NPC286871
0.736	Intermediate Similarity	NPC282092
0.7358	Intermediate Similarity	NPC476326
0.7344	Intermediate Similarity	NPC13367
0.7296	Intermediate Similarity	NPC477159
0.7292	Intermediate Similarity	NPC139085
0.7292	Intermediate Similarity	NPC251212
0.7292	Intermediate Similarity	NPC214626
0.7259	Intermediate Similarity	NPC245741
0.7259	Intermediate Similarity	NPC97584
0.7231	Intermediate Similarity	NPC99043
0.7231	Intermediate Similarity	NPC218594
0.7216	Intermediate Similarity	NPC129624
0.7214	Intermediate Similarity	NPC25401
0.7198	Intermediate Similarity	NPC471436
0.7196	Intermediate Similarity	NPC176983
0.7194	Intermediate Similarity	NPC11149
0.7188	Intermediate Similarity	NPC469915
0.7173	Intermediate Similarity	NPC214960
0.7173	Intermediate Similarity	NPC279527
0.7163	Intermediate Similarity	NPC473837
0.7151	Intermediate Similarity	NPC478076
0.7136	Intermediate Similarity	NPC472209
0.7129	Intermediate Similarity	NPC329833
0.7128	Intermediate Similarity	NPC264482
0.7128	Intermediate Similarity	NPC203202
0.7124	Intermediate Similarity	NPC473565
0.7122	Intermediate Similarity	NPC162440
0.7114	Intermediate Similarity	NPC284706
0.7113	Intermediate Similarity	NPC210415
0.7113	Intermediate Similarity	NPC21752
0.7113	Intermediate Similarity	NPC293255
0.7113	Intermediate Similarity	NPC298851
0.7113	Intermediate Similarity	NPC276993
0.7113	Intermediate Similarity	NPC181138
0.7105	Intermediate Similarity	NPC99632
0.7105	Intermediate Similarity	NPC282339
0.7104	Intermediate Similarity	NPC473458
0.7097	Intermediate Similarity	NPC223590
0.7092	Intermediate Similarity	NPC186669
0.7078	Intermediate Similarity	NPC106593
0.7065	Intermediate Similarity	NPC14994
0.7064	Intermediate Similarity	NPC140311
0.7056	Intermediate Similarity	NPC321211
0.7053	Intermediate Similarity	NPC143457
0.705	Intermediate Similarity	NPC469460
0.705	Intermediate Similarity	NPC322621
0.7047	Intermediate Similarity	NPC469462
0.7005	Intermediate Similarity	NPC260075
0.6995	Remote Similarity	NPC311330
0.6986	Remote Similarity	NPC10653
0.6986	Remote Similarity	NPC318525
0.6985	Remote Similarity	NPC475962
0.6982	Remote Similarity	NPC476436
0.697	Remote Similarity	NPC6974
0.6968	Remote Similarity	NPC473667
0.6954	Remote Similarity	NPC475427
0.6951	Remote Similarity	NPC471513
0.695	Remote Similarity	NPC159963
0.6943	Remote Similarity	NPC52059
0.6943	Remote Similarity	NPC470069
0.6941	Remote Similarity	NPC288110
0.6938	Remote Similarity	NPC138830
0.6907	Remote Similarity	NPC473441
0.6907	Remote Similarity	NPC131273
0.6893	Remote Similarity	NPC470485
0.6884	Remote Similarity	NPC475094
0.6875	Remote Similarity	NPC474058
0.6875	Remote Similarity	NPC73644
0.6872	Remote Similarity	NPC475223
0.6869	Remote Similarity	NPC471950
0.6869	Remote Similarity	NPC471945
0.6861	Remote Similarity	NPC477394
0.6859	Remote Similarity	NPC153694
0.6859	Remote Similarity	NPC211525
0.6857	Remote Similarity	NPC67904
0.6853	Remote Similarity	NPC285622
0.684	Remote Similarity	NPC475448
0.684	Remote Similarity	NPC246983
0.6837	Remote Similarity	NPC471951
0.6837	Remote Similarity	NPC471946
0.6828	Remote Similarity	NPC476429
0.6825	Remote Similarity	NPC176371
0.6825	Remote Similarity	NPC136573
0.6824	Remote Similarity	NPC311451
0.6824	Remote Similarity	NPC329932
0.6823	Remote Similarity	NPC263709
0.6823	Remote Similarity	NPC310403
0.6823	Remote Similarity	NPC97380
0.6823	Remote Similarity	NPC148468
0.6823	Remote Similarity	NPC63210
0.6823	Remote Similarity	NPC243673
0.682	Remote Similarity	NPC127996
0.681	Remote Similarity	NPC107828
0.681	Remote Similarity	NPC469452
0.681	Remote Similarity	NPC469451
0.681	Remote Similarity	NPC90358
0.6808	Remote Similarity	NPC477180
0.6808	Remote Similarity	NPC477181
0.6808	Remote Similarity	NPC477178
0.6808	Remote Similarity	NPC254850
0.6806	Remote Similarity	NPC234999
0.6797	Remote Similarity	NPC469450
0.6797	Remote Similarity	NPC471782
0.6797	Remote Similarity	NPC471583
0.6796	Remote Similarity	NPC470483
0.6792	Remote Similarity	NPC1464
0.6791	Remote Similarity	NPC470491
0.6791	Remote Similarity	NPC475259
0.6776	Remote Similarity	NPC477173
0.6776	Remote Similarity	NPC470490
0.6776	Remote Similarity	NPC477174
0.6769	Remote Similarity	NPC160113
0.6769	Remote Similarity	NPC476220
0.6769	Remote Similarity	NPC471124
0.6768	Remote Similarity	NPC473743
0.6763	Remote Similarity	NPC473004
0.6762	Remote Similarity	NPC112752
0.6762	Remote Similarity	NPC311054
0.6761	Remote Similarity	NPC477179
0.6759	Remote Similarity	NPC477160
0.6753	Remote Similarity	NPC278540
0.6753	Remote Similarity	NPC301501
0.6744	Remote Similarity	NPC470488
0.6743	Remote Similarity	NPC475778
0.6743	Remote Similarity	NPC10732
0.6742	Remote Similarity	NPC77777
0.674	Remote Similarity	NPC477397
0.6739	Remote Similarity	NPC154922
0.6738	Remote Similarity	NPC472100
0.6738	Remote Similarity	NPC264589
0.6736	Remote Similarity	NPC36495
0.6735	Remote Similarity	NPC278887
0.6729	Remote Similarity	NPC87714
0.6728	Remote Similarity	NPC475359
0.6728	Remote Similarity	NPC191817
0.6726	Remote Similarity	NPC183426
0.6718	Remote Similarity	NPC313757
0.6712	Remote Similarity	NPC222046
0.6711	Remote Similarity	NPC231924
0.6703	Remote Similarity	NPC471516
0.6702	Remote Similarity	NPC94602
0.6701	Remote Similarity	NPC248117
0.6701	Remote Similarity	NPC224970
0.6701	Remote Similarity	NPC167724
0.6701	Remote Similarity	NPC223595
0.6699	Remote Similarity	NPC21483
0.6699	Remote Similarity	NPC198205
0.6699	Remote Similarity	NPC243626
0.6698	Remote Similarity	NPC246140
0.6698	Remote Similarity	NPC18661
0.6698	Remote Similarity	NPC195787
0.6696	Remote Similarity	NPC41318
0.6696	Remote Similarity	NPC469312
0.6682	Remote Similarity	NPC469743
0.6682	Remote Similarity	NPC100863
0.6681	Remote Similarity	NPC477393
0.6667	Remote Similarity	NPC159815
0.6667	Remote Similarity	NPC474059
0.6667	Remote Similarity	NPC472118
0.6667	Remote Similarity	NPC161827
0.6652	Remote Similarity	NPC304837
0.6652	Remote Similarity	NPC476258
0.6651	Remote Similarity	NPC184195
0.6651	Remote Similarity	NPC281470

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 NPC475489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	547
0.2-0.3	749
0.3-0.4	2283
0.4-0.5	3941
0.5-0.6	1363
0.6-0.7	79
0.7-0.8	2
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
0.7208	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5741	Approved
0.7204	Intermediate Similarity	NPD5743	Approved
0.7204	Intermediate Similarity	NPD5742	Approved
0.7151	Intermediate Similarity	NPD4121	Phase 3
0.7151	Intermediate Similarity	NPD4120	Approved
0.6963	Remote Similarity	NPD7600	Phase 2
0.695	Remote Similarity	NPD7962	Phase 2
0.6911	Remote Similarity	NPD7599	Phase 2
0.6774	Remote Similarity	NPD7295	Approved
0.672	Remote Similarity	NPD7487	Discontinued
0.6684	Remote Similarity	NPD7606	Phase 3
0.6684	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2820	Phase 3
0.6614	Remote Similarity	NPD7478	Approved
0.6613	Remote Similarity	NPD2365	Approved
0.657	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6805	Discontinued
0.6489	Remote Similarity	NPD7082	Approved
0.6465	Remote Similarity	NPD4601	Approved
0.6465	Remote Similarity	NPD4600	Approved
0.6464	Remote Similarity	NPD2613	Approved
0.6455	Remote Similarity	NPD7259	Approved
0.6418	Remote Similarity	NPD7795	Phase 2
0.6413	Remote Similarity	NPD5182	Approved
0.6413	Remote Similarity	NPD5184	Approved
0.6413	Remote Similarity	NPD5185	Approved
0.6411	Remote Similarity	NPD6891	Phase 2
0.6406	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6995	Phase 1
0.6378	Remote Similarity	NPD7105	Phase 1
0.6378	Remote Similarity	NPD1663	Discontinued
0.6373	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3089	Approved
0.6359	Remote Similarity	NPD2566	Approved
0.6359	Remote Similarity	NPD4746	Phase 3
0.6359	Remote Similarity	NPD2570	Approved
0.6359	Remote Similarity	NPD2573	Approved
0.6359	Remote Similarity	NPD2574	Discontinued
0.6359	Remote Similarity	NPD4745	Approved
0.6359	Remote Similarity	NPD3088	Approved
0.6359	Remote Similarity	NPD2571	Approved
0.6359	Remote Similarity	NPD3614	Approved
0.6359	Remote Similarity	NPD3087	Approved
0.6359	Remote Similarity	NPD3090	Approved
0.6359	Remote Similarity	NPD3615	Approved
0.6359	Remote Similarity	NPD3616	Approved
0.6345	Remote Similarity	NPD8630	Approved
0.6321	Remote Similarity	NPD5942	Approved
0.6321	Remote Similarity	NPD6659	Phase 2
0.6321	Remote Similarity	NPD4682	Phase 2
0.6321	Remote Similarity	NPD5941	Approved
0.6318	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7497	Discontinued
0.6296	Remote Similarity	NPD7777	Approved
0.6296	Remote Similarity	NPD7778	Approved
0.6296	Remote Similarity	NPD53	Approved
0.629	Remote Similarity	NPD4684	Phase 3
0.629	Remote Similarity	NPD4686	Approved
0.629	Remote Similarity	NPD4685	Phase 3
0.6282	Remote Similarity	NPD7688	Phase 1
0.628	Remote Similarity	NPD6879	Phase 2
0.628	Remote Similarity	NPD6878	Phase 2
0.6269	Remote Similarity	NPD8165	Discontinued
0.6269	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5430	Discontinued
0.6267	Remote Similarity	NPD6874	Approved
0.6267	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4216	Approved
0.6257	Remote Similarity	NPD4217	Approved
0.6257	Remote Similarity	NPD3131	Approved
0.6257	Remote Similarity	NPD2610	Approved
0.6257	Remote Similarity	NPD4218	Approved
0.6257	Remote Similarity	NPD2608	Approved
0.6257	Remote Similarity	NPD4215	Approved
0.6257	Remote Similarity	NPD3132	Approved
0.6257	Remote Similarity	NPD2612	Approved
0.6257	Remote Similarity	NPD2611	Approved
0.6257	Remote Similarity	NPD2609	Approved
0.625	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7707	Approved
0.6238	Remote Similarity	NPD5823	Approved
0.6225	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4846	Phase 2
0.6207	Remote Similarity	NPD6457	Approved
0.6204	Remote Similarity	NPD5411	Discontinued
0.6179	Remote Similarity	NPD7683	Discontinued
0.6171	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8240	Discontinued
0.6165	Remote Similarity	NPD3423	Phase 2
0.6165	Remote Similarity	NPD3422	Phase 3
0.6157	Remote Similarity	NPD7878	Phase 2
0.6154	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7205	Discontinued
0.615	Remote Similarity	NPD7301	Phase 3
0.6146	Remote Similarity	NPD5024	Approved
0.6141	Remote Similarity	NPD7576	Discontinued
0.6136	Remote Similarity	NPD6238	Discontinued
0.6134	Remote Similarity	NPD6416	Phase 2
0.6121	Remote Similarity	NPD4499	Approved
0.6117	Remote Similarity	NPD5997	Discontinued
0.6106	Remote Similarity	NPD5600	Discontinued
0.6099	Remote Similarity	NPD7001	Phase 3
0.6098	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7941	Phase 3
0.6081	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD6445	Discontinued
0.6078	Remote Similarity	NPD7805	Phase 3
0.6065	Remote Similarity	NPD7569	Approved
0.6065	Remote Similarity	NPD7570	Approved
0.6065	Remote Similarity	NPD8146	Phase 2
0.6064	Remote Similarity	NPD8416	Discontinued
0.6062	Remote Similarity	NPD4430	Phase 2
0.6059	Remote Similarity	NPD3790	Phase 2
0.6055	Remote Similarity	NPD5582	Discontinued
0.6051	Remote Similarity	NPD3141	Discontinued
0.6042	Remote Similarity	NPD2093	Discontinued
0.6042	Remote Similarity	NPD3625	Discontinued
0.6038	Remote Similarity	NPD7281	Phase 3
0.6038	Remote Similarity	NPD7280	Phase 3
0.6035	Remote Similarity	NPD7595	Discontinued
0.6034	Remote Similarity	NPD3437	Discontinued
0.6032	Remote Similarity	NPD8643	Discontinued
0.6031	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.603	Remote Similarity	NPD5086	Approved
0.603	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5312	Approved
0.6029	Remote Similarity	NPD5313	Approved
0.6029	Remote Similarity	NPD3449	Discontinued
0.6026	Remote Similarity	NPD7820	Phase 3
0.6019	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5466	Approved
0.601	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD8459	Approved
0.6008	Remote Similarity	NPD8460	Approved
0.6008	Remote Similarity	NPD7432	Phase 2
0.6008	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5194	Approved
0.6	Remote Similarity	NPD5725	Approved
0.6	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6073	Approved
0.6	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5196	Approved
0.6	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5197	Approved
0.5991	Remote Similarity	NPD7973	Discontinued
0.5989	Remote Similarity	NPD4766	Approved
0.5989	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7770	Phase 3
0.5982	Remote Similarity	NPD5426	Phase 3
0.598	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6792	Phase 3
0.5974	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7300	Phase 3
0.5973	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD6999	Discontinued
0.5973	Remote Similarity	NPD7302	Phase 3
0.5972	Remote Similarity	NPD5899	Approved
0.5972	Remote Similarity	NPD5898	Approved
0.5972	Remote Similarity	NPD5897	Approved
0.5972	Remote Similarity	NPD3227	Phase 2
0.597	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8374	Phase 3
0.5965	Remote Similarity	NPD7470	Discontinued
0.5965	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5610	Approved
0.5958	Remote Similarity	NPD6723	Discontinued
0.5957	Remote Similarity	NPD3912	Discontinued
0.5956	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.595	Remote Similarity	NPD2790	Discontinued
0.5949	Remote Similarity	NPD2575	Approved
0.5947	Remote Similarity	NPD2791	Discontinued
0.5945	Remote Similarity	NPD5077	Approved
0.5945	Remote Similarity	NPD5504	Discontinued
0.5945	Remote Similarity	NPD5076	Approved
0.5943	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD7944	Discontinued
0.5935	Remote Similarity	NPD6557	Phase 2
0.5931	Remote Similarity	NPD8160	Phase 2
0.593	Remote Similarity	NPD8364	Approved
0.593	Remote Similarity	NPD8363	Approved
0.5926	Remote Similarity	NPD7234	Approved
0.5926	Remote Similarity	NPD7233	Approved
0.5916	Remote Similarity	NPD8467	Approved
0.5916	Remote Similarity	NPD8173	Phase 2
0.5916	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD8465	Approved
0.5916	Remote Similarity	NPD8466	Approved
0.5916	Remote Similarity	NPD8172	Phase 2
0.5914	Remote Similarity	NPD5993	Phase 1
0.5911	Remote Similarity	NPD8468	Phase 2
0.5909	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4432	Discontinued
0.5907	Remote Similarity	NPD7186	Phase 3

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