NPASS Compound

Structure

NPC195636 OpenBabel07101718242D 30 35 0 0 1 0 0 0 0 0999 V2000 -2.5370 -1.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4856 0.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8922 -1.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3586 -4.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5853 -2.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 -0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 -2.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8734 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2003 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7659 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3922 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8855 -2.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3197 -3.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8435 -1.5128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9705 -1.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6284 -2.4341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.4804 -4.1337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 0.4446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 -1.1256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2392 -3.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 -0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 6 7 1 0 0 0 0 7 25 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 1 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 6 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 5 1 1 0 0 0 23 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.2
Volume:	407.788
LogP:	1.883
LogD:	2.081
LogS:	-4.123
# Rotatable Bonds:	5
TPSA:	72.89
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	5.284
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.222
MDCK Permeability:	2.4957937057479285e-05
Pgp-inhibitor:	0.416
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	74.60443878173828%
Volume Distribution (VD):	1.683
Pgp-substrate:	39.148216247558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	8.397
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.793
Human Hepatotoxicity (H-HT):	0.655
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.084
Carcinogencity:	0.754
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC195636

Natural Product ID:	NPC195636
*Common Name:**	10-O-Methyljerantinine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WCCNRTCHONFGMU-WNCSLHQUSA-N
Standard InCHI:	InChI=1S/C23H28N2O5/c1-5-22-10-12(20(26)29-4)18-23(6-7-25(21(22)23)11-17-19(22)30-17)13-8-15(27-2)16(28-3)9-14(13)24-18/h8-9,17,19,21,24H,5-7,10-11H2,1-4H3/t17-,19-,21-,22+,23-/m0/s1
SMILES:	CC[C@@]12CC(=C3[C@]4(CCN(C[C@H]5[C@@H]1O5)[C@@H]24)c1cc(c(cc1N3)OC)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525066
PubChem CID:	25112286
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-type alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7360.0	nM	PMID[555812]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10700.0	nM	PMID[555812]

☑ 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 NPC195636 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	358
0.1-0.2	1709
0.2-0.3	5758
0.3-0.4	11925
0.4-0.5	12546
0.5-0.6	8963
0.6-0.7	1217
0.7-0.8	179
0.8-0.85	32
0.85-0.9	5
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC476069
0.9648	High Similarity	NPC19175
0.9303	High Similarity	NPC128476
0.9231	High Similarity	NPC291173
0.9031	High Similarity	NPC475147
0.8995	High Similarity	NPC269449
0.8966	High Similarity	NPC77777
0.8945	High Similarity	NPC475133
0.8719	High Similarity	NPC119722
0.8708	High Similarity	NPC231924
0.865	High Similarity	NPC87714
0.8551	High Similarity	NPC126556
0.8454	Intermediate Similarity	NPC189661
0.8424	Intermediate Similarity	NPC195787
0.8424	Intermediate Similarity	NPC246140
0.8418	Intermediate Similarity	NPC22476
0.8247	Intermediate Similarity	NPC159963
0.8182	Intermediate Similarity	NPC159815
0.8173	Intermediate Similarity	NPC14994
0.8169	Intermediate Similarity	NPC10653
0.8169	Intermediate Similarity	NPC318525
0.8161	Intermediate Similarity	NPC469722
0.8141	Intermediate Similarity	NPC25401
0.8119	Intermediate Similarity	NPC223242
0.81	Intermediate Similarity	NPC154922
0.808	Intermediate Similarity	NPC477395
0.8063	Intermediate Similarity	NPC131977
0.8045	Intermediate Similarity	NPC139373
0.801	Intermediate Similarity	NPC1464
0.8009	Intermediate Similarity	NPC477393
0.8009	Intermediate Similarity	NPC127996
0.7991	Intermediate Similarity	NPC469450
0.7974	Intermediate Similarity	NPC120239
0.7973	Intermediate Similarity	NPC160113
0.7973	Intermediate Similarity	NPC476220
0.796	Intermediate Similarity	NPC203628
0.7945	Intermediate Similarity	NPC473458
0.7939	Intermediate Similarity	NPC477396
0.792	Intermediate Similarity	NPC469452
0.792	Intermediate Similarity	NPC113455
0.792	Intermediate Similarity	NPC469451
0.791	Intermediate Similarity	NPC5630
0.7874	Intermediate Similarity	NPC232600
0.7867	Intermediate Similarity	NPC301501
0.7857	Intermediate Similarity	NPC186669
0.7851	Intermediate Similarity	NPC329932
0.784	Intermediate Similarity	NPC10732
0.7832	Intermediate Similarity	NPC476258
0.7832	Intermediate Similarity	NPC304837
0.7816	Intermediate Similarity	NPC100863
0.7806	Intermediate Similarity	NPC264482
0.7806	Intermediate Similarity	NPC203202
0.7805	Intermediate Similarity	NPC303214
0.7793	Intermediate Similarity	NPC477397
0.7788	Intermediate Similarity	NPC288110
0.7783	Intermediate Similarity	NPC471513
0.774	Intermediate Similarity	NPC127178
0.7731	Intermediate Similarity	NPC234772
0.7709	Intermediate Similarity	NPC151171
0.7658	Intermediate Similarity	NPC476436
0.7638	Intermediate Similarity	NPC6974
0.7602	Intermediate Similarity	NPC148124
0.7574	Intermediate Similarity	NPC97584
0.7571	Intermediate Similarity	NPC138830
0.7571	Intermediate Similarity	NPC67904
0.756	Intermediate Similarity	NPC218733
0.756	Intermediate Similarity	NPC138615
0.756	Intermediate Similarity	NPC265642
0.756	Intermediate Similarity	NPC132874
0.7557	Intermediate Similarity	NPC99724
0.755	Intermediate Similarity	NPC218594
0.755	Intermediate Similarity	NPC99043
0.7534	Intermediate Similarity	NPC115588
0.7512	Intermediate Similarity	NPC268077
0.7512	Intermediate Similarity	NPC161804
0.75	Intermediate Similarity	NPC243626
0.7489	Intermediate Similarity	NPC476429
0.7477	Intermediate Similarity	NPC46259
0.7477	Intermediate Similarity	NPC477161
0.7476	Intermediate Similarity	NPC141440
0.7467	Intermediate Similarity	NPC248903
0.7466	Intermediate Similarity	NPC222046
0.7465	Intermediate Similarity	NPC207971
0.7465	Intermediate Similarity	NPC82541
0.7463	Intermediate Similarity	NPC21425
0.7454	Intermediate Similarity	NPC477160
0.7426	Intermediate Similarity	NPC35680
0.7422	Intermediate Similarity	NPC26928
0.7421	Intermediate Similarity	NPC87560
0.7416	Intermediate Similarity	NPC230313
0.74	Intermediate Similarity	NPC474708
0.7378	Intermediate Similarity	NPC477394
0.7371	Intermediate Similarity	NPC61013
0.7368	Intermediate Similarity	NPC94499
0.735	Intermediate Similarity	NPC475845
0.7342	Intermediate Similarity	NPC195120
0.7313	Intermediate Similarity	NPC470480
0.7301	Intermediate Similarity	NPC122886
0.73	Intermediate Similarity	NPC57812
0.73	Intermediate Similarity	NPC474324
0.7296	Intermediate Similarity	NPC248117
0.7282	Intermediate Similarity	NPC473007
0.7281	Intermediate Similarity	NPC478075
0.7264	Intermediate Similarity	NPC272706
0.726	Intermediate Similarity	NPC230098
0.7255	Intermediate Similarity	NPC474470
0.7245	Intermediate Similarity	NPC193410
0.724	Intermediate Similarity	NPC268223
0.7238	Intermediate Similarity	NPC63152
0.7238	Intermediate Similarity	NPC473004
0.723	Intermediate Similarity	NPC71124
0.7225	Intermediate Similarity	NPC473008
0.7217	Intermediate Similarity	NPC33256
0.72	Intermediate Similarity	NPC224970
0.72	Intermediate Similarity	NPC167724
0.72	Intermediate Similarity	NPC157983
0.72	Intermediate Similarity	NPC118154
0.72	Intermediate Similarity	NPC223595
0.7195	Intermediate Similarity	NPC470482
0.7195	Intermediate Similarity	NPC470481
0.7194	Intermediate Similarity	NPC123241
0.7192	Intermediate Similarity	NPC65403
0.7186	Intermediate Similarity	NPC475720
0.7186	Intermediate Similarity	NPC474192
0.7184	Intermediate Similarity	NPC474745
0.7177	Intermediate Similarity	NPC162694
0.7172	Intermediate Similarity	NPC293458
0.7156	Intermediate Similarity	NPC219397
0.7155	Intermediate Similarity	NPC473105
0.715	Intermediate Similarity	NPC70290
0.715	Intermediate Similarity	NPC46744
0.715	Intermediate Similarity	NPC124302
0.715	Intermediate Similarity	NPC14622
0.715	Intermediate Similarity	NPC73020
0.715	Intermediate Similarity	NPC215098
0.7149	Intermediate Similarity	NPC21638
0.7143	Intermediate Similarity	NPC474059
0.7136	Intermediate Similarity	NPC474325
0.713	Intermediate Similarity	NPC469732
0.7123	Intermediate Similarity	NPC254957
0.7122	Intermediate Similarity	NPC304675
0.7116	Intermediate Similarity	NPC5374
0.7107	Intermediate Similarity	NPC329982
0.7097	Intermediate Similarity	NPC328700
0.7097	Intermediate Similarity	NPC474077
0.7097	Intermediate Similarity	NPC202771
0.7097	Intermediate Similarity	NPC2173
0.7097	Intermediate Similarity	NPC119818
0.7097	Intermediate Similarity	NPC286135
0.7095	Intermediate Similarity	NPC477186
0.7087	Intermediate Similarity	NPC237044
0.7085	Intermediate Similarity	NPC321166
0.7083	Intermediate Similarity	NPC72788
0.7083	Intermediate Similarity	NPC226652
0.7083	Intermediate Similarity	NPC120671
0.7083	Intermediate Similarity	NPC314100
0.7081	Intermediate Similarity	NPC475981
0.7081	Intermediate Similarity	NPC474746
0.7076	Intermediate Similarity	NPC475816
0.7075	Intermediate Similarity	NPC204970
0.7072	Intermediate Similarity	NPC295479
0.7072	Intermediate Similarity	NPC220241
0.707	Intermediate Similarity	NPC23080
0.707	Intermediate Similarity	NPC193906
0.7063	Intermediate Similarity	NPC471303
0.7061	Intermediate Similarity	NPC284685
0.7059	Intermediate Similarity	NPC168250
0.7056	Intermediate Similarity	NPC88923
0.7056	Intermediate Similarity	NPC315634
0.7056	Intermediate Similarity	NPC100734
0.7048	Intermediate Similarity	NPC181928
0.7048	Intermediate Similarity	NPC214629
0.7035	Intermediate Similarity	NPC182853
0.7033	Intermediate Similarity	NPC102760
0.7032	Intermediate Similarity	NPC470484
0.703	Intermediate Similarity	NPC247972
0.7018	Intermediate Similarity	NPC118189
0.7015	Intermediate Similarity	NPC70172
0.701	Intermediate Similarity	NPC158148
0.701	Intermediate Similarity	NPC266176
0.701	Intermediate Similarity	NPC82533
0.701	Intermediate Similarity	NPC290759
0.7005	Intermediate Similarity	NPC474427
0.6987	Remote Similarity	NPC250960
0.6987	Remote Similarity	NPC71539
0.6981	Remote Similarity	NPC473298
0.6976	Remote Similarity	NPC329338
0.6976	Remote Similarity	NPC469726
0.6974	Remote Similarity	NPC472099
0.6972	Remote Similarity	NPC471512
0.6971	Remote Similarity	NPC15919
0.697	Remote Similarity	NPC266994
0.6964	Remote Similarity	NPC116178
0.696	Remote Similarity	NPC96321
0.696	Remote Similarity	NPC473041
0.6957	Remote Similarity	NPC287152
0.6944	Remote Similarity	NPC475713
0.6944	Remote Similarity	NPC474432
0.6943	Remote Similarity	NPC76478
0.6942	Remote Similarity	NPC225597

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 NPC195636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	610
0.2-0.3	841
0.3-0.4	2095
0.4-0.5	2873
0.5-0.6	2078
0.6-0.7	434
0.7-0.8	15
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
0.7768	Intermediate Similarity	NPD6625	Approved
0.7381	Intermediate Similarity	NPD5582	Discontinued
0.7336	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4859	Phase 1
0.715	Intermediate Similarity	NPD5071	Phase 2
0.715	Intermediate Similarity	NPD4420	Approved
0.7143	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3592	Approved
0.7136	Intermediate Similarity	NPD3591	Approved
0.7114	Intermediate Similarity	NPD6107	Approved
0.7097	Intermediate Similarity	NPD5005	Approved
0.7097	Intermediate Similarity	NPD5006	Approved
0.7094	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD683	Approved
0.7061	Intermediate Similarity	NPD7955	Approved
0.7061	Intermediate Similarity	NPD7956	Approved
0.7056	Intermediate Similarity	NPD7803	Approved
0.7054	Intermediate Similarity	NPD7559	Phase 2
0.7053	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7278	Phase 2
0.7031	Intermediate Similarity	NPD7279	Phase 2
0.7004	Intermediate Similarity	NPD2899	Discontinued
0.6995	Remote Similarity	NPD5183	Approved
0.6995	Remote Similarity	NPD5186	Approved
0.6991	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5313	Approved
0.699	Remote Similarity	NPD5312	Approved
0.6981	Remote Similarity	NPD2845	Phase 2
0.6981	Remote Similarity	NPD2843	Phase 2
0.6974	Remote Similarity	NPD3437	Discontinued
0.6972	Remote Similarity	NPD6238	Discontinued
0.6968	Remote Similarity	NPD4596	Phase 1
0.6964	Remote Similarity	NPD4492	Approved
0.6964	Remote Similarity	NPD4494	Approved
0.6937	Remote Similarity	NPD4082	Approved
0.6936	Remote Similarity	NPD6723	Discontinued
0.6927	Remote Similarity	NPD4107	Approved
0.692	Remote Similarity	NPD4493	Discontinued
0.6905	Remote Similarity	NPD2971	Approved
0.6905	Remote Similarity	NPD2968	Approved
0.6904	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7186	Phase 3
0.6895	Remote Similarity	NPD7708	Approved
0.6883	Remote Similarity	NPD3912	Discontinued
0.6881	Remote Similarity	NPD3297	Approved
0.6872	Remote Similarity	NPD6853	Approved
0.6872	Remote Similarity	NPD6851	Approved
0.6866	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3472	Approved
0.6861	Remote Similarity	NPD4022	Approved
0.6858	Remote Similarity	NPD4455	Discontinued
0.6849	Remote Similarity	NPD4846	Phase 2
0.6845	Remote Similarity	NPD4481	Phase 3
0.6827	Remote Similarity	NPD5600	Discontinued
0.6818	Remote Similarity	NPD4482	Phase 3
0.6814	Remote Similarity	NPD3888	Discontinued
0.6809	Remote Similarity	NPD8466	Approved
0.6809	Remote Similarity	NPD8465	Approved
0.6809	Remote Similarity	NPD8467	Approved
0.6802	Remote Similarity	NPD3298	Approved
0.6802	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3372	Discontinued
0.68	Remote Similarity	NPD3893	Discontinued
0.6789	Remote Similarity	NPD2973	Approved
0.6789	Remote Similarity	NPD2975	Approved
0.6789	Remote Similarity	NPD2974	Approved
0.6789	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5658	Approved
0.6773	Remote Similarity	NPD4580	Approved
0.6772	Remote Similarity	NPD8364	Approved
0.6772	Remote Similarity	NPD8363	Approved
0.677	Remote Similarity	NPD1945	Phase 1
0.6762	Remote Similarity	NPD6297	Approved
0.6761	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4885	Approved
0.6746	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7476	Discontinued
0.6736	Remote Similarity	NPD3006	Discontinued
0.6729	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4040	Phase 1
0.6726	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD8149	Discontinued
0.6719	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3442	Approved
0.6709	Remote Similarity	NPD3441	Approved
0.6705	Remote Similarity	NPD8426	Approved
0.6705	Remote Similarity	NPD8460	Approved
0.6705	Remote Similarity	NPD8459	Approved
0.6705	Remote Similarity	NPD8425	Approved
0.6699	Remote Similarity	NPD2247	Approved
0.6699	Remote Similarity	NPD2680	Approved
0.6699	Remote Similarity	NPD2681	Approved
0.6699	Remote Similarity	NPD2249	Approved
0.6698	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6997	Phase 2
0.6683	Remote Similarity	NPD2246	Approved
0.6683	Remote Similarity	NPD1769	Discontinued
0.6683	Remote Similarity	NPD2248	Approved
0.6682	Remote Similarity	NPD3633	Approved
0.6682	Remote Similarity	NPD3634	Approved
0.6681	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8428	Approved
0.668	Remote Similarity	NPD8429	Approved
0.668	Remote Similarity	NPD8427	Approved
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD3450	Approved
0.6667	Remote Similarity	NPD6517	Phase 3
0.6667	Remote Similarity	NPD7827	Phase 1
0.6653	Remote Similarity	NPD7560	Approved
0.6653	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4583	Approved
0.6652	Remote Similarity	NPD7891	Discontinued
0.6652	Remote Similarity	NPD4582	Approved
0.6651	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD2907	Approved
0.6637	Remote Similarity	NPD2906	Approved
0.6637	Remote Similarity	NPD3516	Approved
0.6637	Remote Similarity	NPD3515	Approved
0.6636	Remote Similarity	NPD2488	Approved
0.6636	Remote Similarity	NPD2490	Approved
0.6635	Remote Similarity	NPD5242	Approved
0.6623	Remote Similarity	NPD5676	Approved
0.6621	Remote Similarity	NPD7256	Discontinued
0.6619	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3983	Phase 3
0.6618	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6457	Approved
0.6609	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4004	Approved
0.6607	Remote Similarity	NPD4002	Approved
0.6607	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6877	Discontinued
0.6605	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4796	Discontinued
0.66	Remote Similarity	NPD3641	Approved
0.66	Remote Similarity	NPD3639	Approved
0.66	Remote Similarity	NPD3640	Phase 3
0.6597	Remote Similarity	NPD6199	Discontinued
0.6595	Remote Similarity	NPD5632	Approved
0.6593	Remote Similarity	NPD7263	Phase 2
0.6591	Remote Similarity	NPD3964	Approved
0.6591	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4166	Phase 2
0.6585	Remote Similarity	NPD1743	Approved
0.6585	Remote Similarity	NPD19	Approved
0.6585	Remote Similarity	NPD1742	Approved
0.658	Remote Similarity	NPD5562	Approved
0.658	Remote Similarity	NPD5561	Approved
0.6579	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5860	Discontinued
0.6578	Remote Similarity	NPD6644	Discontinued
0.6577	Remote Similarity	NPD6874	Approved
0.657	Remote Similarity	NPD7048	Phase 3
0.6567	Remote Similarity	NPD5496	Approved
0.6562	Remote Similarity	NPD3057	Approved
0.6562	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8358	Approved
0.6557	Remote Similarity	NPD7479	Phase 2
0.6556	Remote Similarity	NPD6963	Approved
0.6556	Remote Similarity	NPD6964	Approved
0.6553	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5980	Discovery
0.6552	Remote Similarity	NPD6386	Approved
0.6552	Remote Similarity	NPD6385	Approved
0.655	Remote Similarity	NPD4206	Approved
0.6549	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4668	Phase 2
0.6528	Remote Similarity	NPD6340	Approved
0.6528	Remote Similarity	NPD6339	Approved
0.6527	Remote Similarity	NPD4952	Phase 3
0.6527	Remote Similarity	NPD4981	Phase 2
0.6517	Remote Similarity	NPD6031	Approved
0.6517	Remote Similarity	NPD6030	Approved
0.6515	Remote Similarity	NPD6494	Phase 2
0.6514	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7281	Phase 3
0.6512	Remote Similarity	NPD7280	Phase 3
0.6512	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD7805	Phase 3
0.6506	Remote Similarity	NPD5482	Discontinued
0.65	Remote Similarity	NPD3631	Phase 3
0.6498	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6228	Discontinued
0.6489	Remote Similarity	NPD3533	Approved
0.6489	Remote Similarity	NPD2972	Approved
0.6485	Remote Similarity	NPD4210	Discontinued
0.6484	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8091	Phase 3
0.6481	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5680	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data