NPASS Compound

Structure

NPC474059 OpenBabel07101719152D 28 31 0 0 1 0 0 0 0 0999 V2000 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8171 -3.1910 0.0000 C 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 3.5491 -4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 13 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 1 0 0 0 17 11 1 1 0 0 0 17 22 1 0 0 0 0 18 12 1 6 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 22 24 1 0 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.23
Volume:	405.114
LogP:	3.825
LogD:	3.679
LogS:	-4.826
# Rotatable Bonds:	5
TPSA:	67.79
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.715
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.699
MDCK Permeability:	1.4889371414028574e-05
Pgp-inhibitor:	0.455
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.27
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.359

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.658
Plasma Protein Binding (PPB):	90.31336212158203%
Volume Distribution (VD):	0.96
Pgp-substrate:	4.6956939697265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.78
CYP2C9-substrate:	0.489
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.813

ADMET: Excretion

Clearance (CL):	6.726
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.358
Drug-inuced Liver Injury (DILI):	0.521
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.802
Skin Sensitization:	0.049
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC474059

Natural Product ID:	NPC474059
*Common Name:**	9-Methoxy 16(R),E-Isositsirikine
IUPAC Name:	methyl (2R)-2-[(2R,3E,11bR)-3-ethylidene-7-methoxy-1,2,4,4a,5,6,6a,11,11a,11b-decahydrobenzo[a]carbazol-2-yl]-3-hydroxypropanoate
Synonyms:	9-Methoxy 16(R),E-Isositsirikine
Standard InCHIKey:	PGOBOWWFWXOGHZ-FCJHPKDCSA-N
Standard InCHI:	InChI=1S/C23H31NO4/c1-4-13-10-14-8-9-15-21-19(6-5-7-20(21)27-2)24-22(15)17(14)11-16(13)18(12-25)23(26)28-3/h4-7,14-18,22,24-25H,8-12H2,1-3H3/b13-4+/t14?,15?,16-,17+,18-,22?/m0/s1
SMILES:	COC(=O)[C@H]([C@H]1C[C@@H]2C(C/C/1=CC)CCC1C2Nc2c1c(OC)ccc2)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459422
PubChem CID:	44559928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33506	strychnos lucens	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]

☑ 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	3
Others	3

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13600.0	nM	PMID[569814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9900.0	nM	PMID[569814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12500.0	nM	PMID[569814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	34600.0	nM	PMID[569814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	36300.0	nM	PMID[569814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	37800.0	nM	PMID[569814]

☑ 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 NPC474059 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	245
0.1-0.2	1139
0.2-0.3	3946
0.3-0.4	12086
0.4-0.5	8926
0.5-0.6	14136
0.6-0.7	2068
0.7-0.8	149
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8085	Intermediate Similarity	NPC230313
0.799	Intermediate Similarity	NPC87714
0.7989	Intermediate Similarity	NPC243626
0.7927	Intermediate Similarity	NPC232600
0.7926	Intermediate Similarity	NPC22476
0.7919	Intermediate Similarity	NPC477160
0.7833	Intermediate Similarity	NPC288110
0.78	Intermediate Similarity	NPC127996
0.7766	Intermediate Similarity	NPC21425
0.776	Intermediate Similarity	NPC303214
0.7754	Intermediate Similarity	NPC473007
0.7737	Intermediate Similarity	NPC28510
0.7737	Intermediate Similarity	NPC203628
0.7696	Intermediate Similarity	NPC473004
0.7692	Intermediate Similarity	NPC67904
0.7685	Intermediate Similarity	NPC234772
0.7684	Intermediate Similarity	NPC473008
0.768	Intermediate Similarity	NPC100863
0.7677	Intermediate Similarity	NPC477161
0.7659	Intermediate Similarity	NPC222046
0.7638	Intermediate Similarity	NPC478075
0.7635	Intermediate Similarity	NPC189661
0.7626	Intermediate Similarity	NPC475147
0.7624	Intermediate Similarity	NPC119722
0.7571	Intermediate Similarity	NPC473458
0.7566	Intermediate Similarity	NPC52262
0.754	Intermediate Similarity	NPC70092
0.7525	Intermediate Similarity	NPC269449
0.7513	Intermediate Similarity	NPC138830
0.75	Intermediate Similarity	NPC246140
0.75	Intermediate Similarity	NPC195787
0.75	Intermediate Similarity	NPC5630
0.7475	Intermediate Similarity	NPC475133
0.7452	Intermediate Similarity	NPC10653
0.7452	Intermediate Similarity	NPC318525
0.745	Intermediate Similarity	NPC14339
0.744	Intermediate Similarity	NPC77777
0.7427	Intermediate Similarity	NPC152768
0.7427	Intermediate Similarity	NPC148183
0.7411	Intermediate Similarity	NPC23080
0.7411	Intermediate Similarity	NPC17677
0.7411	Intermediate Similarity	NPC193906
0.7406	Intermediate Similarity	NPC471513
0.7393	Intermediate Similarity	NPC231924
0.7391	Intermediate Similarity	NPC126556
0.7376	Intermediate Similarity	NPC198160
0.7366	Intermediate Similarity	NPC10732
0.7366	Intermediate Similarity	NPC159815
0.7337	Intermediate Similarity	NPC127178
0.733	Intermediate Similarity	NPC217903
0.7282	Intermediate Similarity	NPC1820
0.7282	Intermediate Similarity	NPC116178
0.7273	Intermediate Similarity	NPC472191
0.7268	Intermediate Similarity	NPC25961
0.7268	Intermediate Similarity	NPC477186
0.7251	Intermediate Similarity	NPC128476
0.7249	Intermediate Similarity	NPC127082
0.7246	Intermediate Similarity	NPC321166
0.7231	Intermediate Similarity	NPC473569
0.7222	Intermediate Similarity	NPC162653
0.7214	Intermediate Similarity	NPC471489
0.7204	Intermediate Similarity	NPC174760
0.7202	Intermediate Similarity	NPC275132
0.7198	Intermediate Similarity	NPC469428
0.719	Intermediate Similarity	NPC473041
0.7182	Intermediate Similarity	NPC151171
0.7178	Intermediate Similarity	NPC1464
0.7176	Intermediate Similarity	NPC477397
0.7172	Intermediate Similarity	NPC469816
0.7172	Intermediate Similarity	NPC469815
0.7169	Intermediate Similarity	NPC154922
0.7162	Intermediate Similarity	NPC469722
0.7162	Intermediate Similarity	NPC469452
0.7157	Intermediate Similarity	NPC204970
0.7157	Intermediate Similarity	NPC206109
0.7157	Intermediate Similarity	NPC114039
0.7156	Intermediate Similarity	NPC473105
0.715	Intermediate Similarity	NPC179704
0.715	Intermediate Similarity	NPC115588
0.715	Intermediate Similarity	NPC19175
0.7149	Intermediate Similarity	NPC478080
0.7143	Intermediate Similarity	NPC195636
0.7143	Intermediate Similarity	NPC169402
0.7136	Intermediate Similarity	NPC46990
0.7121	Intermediate Similarity	NPC203972
0.712	Intermediate Similarity	NPC321211
0.7114	Intermediate Similarity	NPC241263
0.711	Intermediate Similarity	NPC474192
0.711	Intermediate Similarity	NPC475720
0.7104	Intermediate Similarity	NPC301501
0.71	Intermediate Similarity	NPC90967
0.7098	Intermediate Similarity	NPC329932
0.7097	Intermediate Similarity	NPC299582
0.7094	Intermediate Similarity	NPC473005
0.7094	Intermediate Similarity	NPC288759
0.7087	Intermediate Similarity	NPC100573
0.7087	Intermediate Similarity	NPC207873
0.7085	Intermediate Similarity	NPC477395
0.7081	Intermediate Similarity	NPC282339
0.7081	Intermediate Similarity	NPC199737
0.7081	Intermediate Similarity	NPC473006
0.7081	Intermediate Similarity	NPC99632
0.7077	Intermediate Similarity	NPC276674
0.7077	Intermediate Similarity	NPC33902
0.7074	Intermediate Similarity	NPC471778
0.7074	Intermediate Similarity	NPC195392
0.7072	Intermediate Similarity	NPC469450
0.707	Intermediate Similarity	NPC122886
0.7068	Intermediate Similarity	NPC285941
0.7065	Intermediate Similarity	NPC132874
0.7065	Intermediate Similarity	NPC138615
0.7065	Intermediate Similarity	NPC218733
0.7065	Intermediate Similarity	NPC29647
0.7065	Intermediate Similarity	NPC265642
0.7062	Intermediate Similarity	NPC97584
0.7056	Intermediate Similarity	NPC283207
0.7056	Intermediate Similarity	NPC474904
0.7056	Intermediate Similarity	NPC148124
0.705	Intermediate Similarity	NPC125924
0.7048	Intermediate Similarity	NPC116238
0.7043	Intermediate Similarity	NPC204867
0.7042	Intermediate Similarity	NPC476069
0.7042	Intermediate Similarity	NPC150239
0.7037	Intermediate Similarity	NPC469671
0.7037	Intermediate Similarity	NPC126676
0.7035	Intermediate Similarity	NPC302001
0.7031	Intermediate Similarity	NPC99043
0.7031	Intermediate Similarity	NPC218594
0.703	Intermediate Similarity	NPC212163
0.7028	Intermediate Similarity	NPC96321
0.7027	Intermediate Similarity	NPC79328
0.7026	Intermediate Similarity	NPC249405
0.7024	Intermediate Similarity	NPC313112
0.7024	Intermediate Similarity	NPC268077
0.7024	Intermediate Similarity	NPC301292
0.7022	Intermediate Similarity	NPC477393
0.7019	Intermediate Similarity	NPC474366
0.7014	Intermediate Similarity	NPC291173
0.701	Intermediate Similarity	NPC15987
0.701	Intermediate Similarity	NPC477159
0.701	Intermediate Similarity	NPC474077
0.7009	Intermediate Similarity	NPC329830
0.7009	Intermediate Similarity	NPC113455
0.7009	Intermediate Similarity	NPC469451
0.7009	Intermediate Similarity	NPC99724
0.7005	Intermediate Similarity	NPC320088
0.7005	Intermediate Similarity	NPC90185
0.7005	Intermediate Similarity	NPC470480
0.7005	Intermediate Similarity	NPC70172
0.7005	Intermediate Similarity	NPC475910
0.6995	Remote Similarity	NPC219397
0.6995	Remote Similarity	NPC287588
0.6991	Remote Similarity	NPC21638
0.699	Remote Similarity	NPC475981
0.699	Remote Similarity	NPC474746
0.6989	Remote Similarity	NPC176983
0.6986	Remote Similarity	NPC87413
0.6982	Remote Similarity	NPC131977
0.698	Remote Similarity	NPC234933
0.6979	Remote Similarity	NPC477187
0.6976	Remote Similarity	NPC207971
0.6973	Remote Similarity	NPC63210
0.6973	Remote Similarity	NPC97380
0.6973	Remote Similarity	NPC263709
0.6973	Remote Similarity	NPC310403
0.6973	Remote Similarity	NPC148468
0.6973	Remote Similarity	NPC243673
0.697	Remote Similarity	NPC22689
0.697	Remote Similarity	NPC312531
0.697	Remote Similarity	NPC105055
0.697	Remote Similarity	NPC174629
0.6968	Remote Similarity	NPC472114
0.6968	Remote Similarity	NPC472115
0.6965	Remote Similarity	NPC473375
0.6965	Remote Similarity	NPC97100
0.6963	Remote Similarity	NPC472099
0.6961	Remote Similarity	NPC472330
0.6961	Remote Similarity	NPC472329
0.6961	Remote Similarity	NPC295676
0.696	Remote Similarity	NPC477396
0.6959	Remote Similarity	NPC294790
0.6959	Remote Similarity	NPC190461
0.6959	Remote Similarity	NPC118633
0.6959	Remote Similarity	NPC148693
0.6957	Remote Similarity	NPC212123
0.6952	Remote Similarity	NPC470481
0.6952	Remote Similarity	NPC470482
0.695	Remote Similarity	NPC470485
0.695	Remote Similarity	NPC471825
0.6948	Remote Similarity	NPC247803
0.6947	Remote Similarity	NPC474814
0.6947	Remote Similarity	NPC112336
0.6946	Remote Similarity	NPC90358
0.6946	Remote Similarity	NPC107828
0.6942	Remote Similarity	NPC470484
0.6941	Remote Similarity	NPC223242
0.6939	Remote Similarity	NPC322621
0.6938	Remote Similarity	NPC471304
0.6937	Remote Similarity	NPC473187
0.6935	Remote Similarity	NPC248117

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 NPC474059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	517
0.2-0.3	764
0.3-0.4	1408
0.4-0.5	2472
0.5-0.6	2884
0.6-0.7	914
0.7-0.8	27
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
0.7869	Intermediate Similarity	NPD7479	Phase 2
0.7772	Intermediate Similarity	NPD4668	Phase 2
0.7657	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD6238	Discontinued
0.7629	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5928	Phase 1
0.7452	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6874	Approved
0.7322	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6723	Discontinued
0.7313	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6457	Approved
0.7286	Intermediate Similarity	NPD3437	Discontinued
0.7258	Intermediate Similarity	NPD5183	Approved
0.7258	Intermediate Similarity	NPD5186	Approved
0.7249	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5496	Approved
0.7236	Intermediate Similarity	NPD5196	Approved
0.7236	Intermediate Similarity	NPD5197	Approved
0.7236	Intermediate Similarity	NPD5194	Approved
0.7208	Intermediate Similarity	NPD5610	Approved
0.7202	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3912	Discontinued
0.7181	Intermediate Similarity	NPD2248	Approved
0.7181	Intermediate Similarity	NPD2246	Approved
0.7176	Intermediate Similarity	NPD4981	Phase 2
0.7171	Intermediate Similarity	NPD2916	Discontinued
0.7171	Intermediate Similarity	NPD4859	Phase 1
0.7158	Intermediate Similarity	NPD2842	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3793	Phase 3
0.7158	Intermediate Similarity	NPD5560	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5937	Approved
0.7136	Intermediate Similarity	NPD8249	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1913	Phase 1
0.7121	Intermediate Similarity	NPD4539	Phase 1
0.7108	Intermediate Similarity	NPD1294	Discontinued
0.7085	Intermediate Similarity	NPD7256	Discontinued
0.7077	Intermediate Similarity	NPD3153	Approved
0.7077	Intermediate Similarity	NPD3154	Approved
0.7073	Intermediate Similarity	NPD3003	Approved
0.7056	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7880	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7476	Discontinued
0.7037	Intermediate Similarity	NPD2215	Approved
0.7037	Intermediate Similarity	NPD2216	Approved
0.7028	Intermediate Similarity	NPD5632	Approved
0.7026	Intermediate Similarity	NPD8167	Discontinued
0.702	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4979	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4493	Discontinued
0.6986	Remote Similarity	NPD1945	Phase 1
0.697	Remote Similarity	NPD7628	Phase 3
0.697	Remote Similarity	NPD7630	Phase 3
0.697	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5903	Approved
0.6967	Remote Similarity	NPD5902	Approved
0.6965	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD955	Approved
0.695	Remote Similarity	NPD7262	Phase 1
0.695	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4590	Approved
0.6942	Remote Similarity	NPD4467	Phase 2
0.6942	Remote Similarity	NPD6644	Discontinued
0.6942	Remote Similarity	NPD4465	Phase 2
0.6931	Remote Similarity	NPD4604	Approved
0.6931	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3983	Phase 3
0.6931	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4605	Approved
0.6931	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5160	Discontinued
0.6927	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4082	Approved
0.6919	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6297	Approved
0.6904	Remote Similarity	NPD6339	Approved
0.6904	Remote Similarity	NPD6340	Approved
0.6902	Remote Similarity	NPD5617	Suspended
0.6898	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6747	Phase 1
0.6895	Remote Similarity	NPD1839	Phase 1
0.6891	Remote Similarity	NPD5600	Discontinued
0.6888	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2845	Phase 2
0.6884	Remote Similarity	NPD2843	Phase 2
0.6878	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6037	Discontinued
0.6875	Remote Similarity	NPD5466	Approved
0.6872	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4492	Approved
0.6872	Remote Similarity	NPD7301	Phase 3
0.6872	Remote Similarity	NPD5754	Discontinued
0.6872	Remote Similarity	NPD4494	Approved
0.6869	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5150	Phase 2
0.6865	Remote Similarity	NPD6677	Suspended
0.6863	Remote Similarity	NPD1768	Approved
0.6862	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4083	Discontinued
0.6857	Remote Similarity	NPD3893	Discontinued
0.6856	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6853	Approved
0.6853	Remote Similarity	NPD6851	Approved
0.685	Remote Similarity	NPD5641	Discontinued
0.6848	Remote Similarity	NPD5811	Approved
0.6847	Remote Similarity	NPD5195	Discontinued
0.6847	Remote Similarity	NPD5003	Discontinued
0.6845	Remote Similarity	NPD3560	Approved
0.6845	Remote Similarity	NPD3556	Approved
0.6845	Remote Similarity	NPD3558	Approved
0.6845	Remote Similarity	NPD3557	Approved
0.6845	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3511	Discontinued
0.6842	Remote Similarity	NPD5488	Discontinued
0.6839	Remote Similarity	NPD6620	Discovery
0.6838	Remote Similarity	NPD7955	Approved
0.6838	Remote Similarity	NPD7956	Approved
0.6837	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6519	Phase 2
0.6828	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4796	Discontinued
0.6825	Remote Similarity	NPD6315	Phase 2
0.6822	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7417	Discontinued
0.6809	Remote Similarity	NPD19	Approved
0.6809	Remote Similarity	NPD1743	Approved
0.6809	Remote Similarity	NPD1742	Approved
0.6808	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD4679	Discontinued
0.6804	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4258	Approved
0.68	Remote Similarity	NPD4259	Approved
0.6792	Remote Similarity	NPD7069	Discontinued
0.6789	Remote Similarity	NPD5823	Approved
0.6788	Remote Similarity	NPD7324	Discontinued
0.678	Remote Similarity	NPD822	Approved
0.6779	Remote Similarity	NPD3298	Approved
0.6776	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2672	Discontinued
0.6771	Remote Similarity	NPD4373	Phase 2
0.6765	Remote Similarity	NPD2941	Discontinued
0.6763	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7626	Approved
0.6763	Remote Similarity	NPD7627	Approved
0.6757	Remote Similarity	NPD6357	Discontinued
0.6754	Remote Similarity	NPD6107	Approved
0.6751	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8364	Approved
0.675	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8363	Approved
0.6743	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4727	Phase 1
0.6739	Remote Similarity	NPD7427	Discontinued
0.6737	Remote Similarity	NPD5430	Discontinued
0.6736	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6967	Phase 2
0.6731	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4710	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7528	Approved
0.6718	Remote Similarity	NPD5810	Discontinued
0.6717	Remote Similarity	NPD7280	Phase 3
0.6717	Remote Similarity	NPD7281	Phase 3
0.6715	Remote Similarity	NPD6321	Discontinued
0.6714	Remote Similarity	NPD7827	Phase 1
0.6713	Remote Similarity	NPD6985	Discontinued
0.6712	Remote Similarity	NPD4952	Phase 3
0.6704	Remote Similarity	NPD7753	Approved
0.6704	Remote Similarity	NPD7752	Approved
0.6703	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3141	Discontinued
0.6703	Remote Similarity	NPD6666	Approved
0.6703	Remote Similarity	NPD6667	Approved
0.6702	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2359	Approved
0.6701	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5938	Phase 3
0.6701	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4587	Phase 3
0.6699	Remote Similarity	NPD5609	Approved
0.6699	Remote Similarity	NPD6250	Discontinued
0.6699	Remote Similarity	NPD3297	Approved
0.6699	Remote Similarity	NPD7891	Discontinued
0.6699	Remote Similarity	NPD5608	Approved
0.6699	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7805	Phase 3
0.6695	Remote Similarity	NPD7803	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