NPASS Compound

Structure

CID128698 OpenBabel06191715482D 24 28 0 0 1 0 0 0 0 0999 V2000 1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 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 -2.5981 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -4.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 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 3 4 1 0 0 0 0 3 13 2 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 6 0 0 0 15 4 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 21 1 1 0 0 0 17 20 1 1 0 0 0 18 21 1 1 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 2 1 1 0 0 0 21 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.24
Volume:	352.294
LogP:	3.849
LogD:	3.756
LogS:	-4.787
# Rotatable Bonds:	0
TPSA:	52.32
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	5.147
Fsp3:	0.857
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:	-4.691
MDCK Permeability:	3.8241571019170806e-05
Pgp-inhibitor:	0.927
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.078
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	81.08721160888672%
Volume Distribution (VD):	1.001
Pgp-substrate:	12.903909683227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.61
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	9.54
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.949
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.957
Carcinogencity:	0.709
Eye Corrosion:	0.225
Eye Irritation:	0.04
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC128698

Natural Product ID:	NPC128698
*Common Name:**	Gitingensine
IUPAC Name:	n.a.
Synonyms:	Gitingensine
Standard InCHIKey:	LFGPYDIPRZAYQB-KWUKWGFESA-N
Standard InCHI:	InChI=1S/C21H31NO2/c1-12-16-5-6-18-15-4-3-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)19(23)24-12/h3,12,14-18H,4-11,22H2,1-2H3/t12-,14+,15+,16+,17-,18-,20-,21-/m0/s1
SMILES:	C[C@H]1[C@H]2CC[C@H]3[C@@H]4CC=C5C[C@@H](CC[C@]5(C)[C@H]4CC[C@]23C(=O)O1)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801974
PubChem CID:	53262720
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443172]
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21443172]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	21000.0	nM	PMID[473479]

☑ 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 NPC128698 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	96
0.1-0.2	740
0.2-0.3	6837
0.3-0.4	16619
0.4-0.5	8361
0.5-0.6	7484
0.6-0.7	2433
0.7-0.8	111
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239768
0.9485	High Similarity	NPC233256
0.9485	High Similarity	NPC195841
0.88	High Similarity	NPC119329
0.844	Intermediate Similarity	NPC35037
0.8333	Intermediate Similarity	NPC98765
0.8191	Intermediate Similarity	NPC470223
0.8131	Intermediate Similarity	NPC79238
0.8125	Intermediate Similarity	NPC28227
0.8085	Intermediate Similarity	NPC100391
0.8037	Intermediate Similarity	NPC63511
0.8037	Intermediate Similarity	NPC472313
0.7979	Intermediate Similarity	NPC21667
0.7963	Intermediate Similarity	NPC474459
0.789	Intermediate Similarity	NPC474452
0.7835	Intermediate Similarity	NPC167877
0.783	Intermediate Similarity	NPC86906
0.78	Intermediate Similarity	NPC470224
0.7732	Intermediate Similarity	NPC264127
0.7629	Intermediate Similarity	NPC323765
0.7576	Intermediate Similarity	NPC472220
0.7576	Intermediate Similarity	NPC97884
0.7573	Intermediate Similarity	NPC322063
0.7551	Intermediate Similarity	NPC470050
0.7551	Intermediate Similarity	NPC470051
0.7551	Intermediate Similarity	NPC195640
0.7549	Intermediate Similarity	NPC56525
0.75	Intermediate Similarity	NPC475894
0.7474	Intermediate Similarity	NPC170038
0.7447	Intermediate Similarity	NPC35574
0.7429	Intermediate Similarity	NPC271387
0.7429	Intermediate Similarity	NPC153792
0.7426	Intermediate Similarity	NPC471896
0.7426	Intermediate Similarity	NPC84171
0.74	Intermediate Similarity	NPC474845
0.7374	Intermediate Similarity	NPC155011
0.7368	Intermediate Similarity	NPC44083
0.7368	Intermediate Similarity	NPC153987
0.7368	Intermediate Similarity	NPC118987
0.7353	Intermediate Similarity	NPC218301
0.7353	Intermediate Similarity	NPC154101
0.7327	Intermediate Similarity	NPC474570
0.732	Intermediate Similarity	NPC240302
0.7308	Intermediate Similarity	NPC469599
0.73	Intermediate Similarity	NPC142361
0.73	Intermediate Similarity	NPC474684
0.7273	Intermediate Similarity	NPC478136
0.7273	Intermediate Similarity	NPC75810
0.7255	Intermediate Similarity	NPC175628
0.7255	Intermediate Similarity	NPC111585
0.7255	Intermediate Similarity	NPC148414
0.7245	Intermediate Similarity	NPC470047
0.7245	Intermediate Similarity	NPC470046
0.7238	Intermediate Similarity	NPC307164
0.7234	Intermediate Similarity	NPC41017
0.7228	Intermediate Similarity	NPC226863
0.7216	Intermediate Similarity	NPC147066
0.7216	Intermediate Similarity	NPC475665
0.7216	Intermediate Similarity	NPC474955
0.7212	Intermediate Similarity	NPC472223
0.7212	Intermediate Similarity	NPC159410
0.7212	Intermediate Similarity	NPC472224
0.7184	Intermediate Similarity	NPC49420
0.7184	Intermediate Similarity	NPC150383
0.7184	Intermediate Similarity	NPC26888
0.7172	Intermediate Similarity	NPC109512
0.7172	Intermediate Similarity	NPC139566
0.7172	Intermediate Similarity	NPC165064
0.717	Intermediate Similarity	NPC292133
0.7158	Intermediate Similarity	NPC472300
0.7157	Intermediate Similarity	NPC475921
0.7157	Intermediate Similarity	NPC474704
0.7157	Intermediate Similarity	NPC474889
0.7156	Intermediate Similarity	NPC36688
0.7156	Intermediate Similarity	NPC140723
0.7156	Intermediate Similarity	NPC36321
0.7143	Intermediate Similarity	NPC100297
0.7129	Intermediate Similarity	NPC96496
0.7129	Intermediate Similarity	NPC187376
0.7129	Intermediate Similarity	NPC159046
0.7129	Intermediate Similarity	NPC233836
0.7117	Intermediate Similarity	NPC244982
0.7117	Intermediate Similarity	NPC476756
0.7115	Intermediate Similarity	NPC470376
0.7115	Intermediate Similarity	NPC170220
0.7115	Intermediate Similarity	NPC63118
0.7115	Intermediate Similarity	NPC49776
0.7115	Intermediate Similarity	NPC470375
0.7115	Intermediate Similarity	NPC474436
0.7115	Intermediate Similarity	NPC141497
0.7115	Intermediate Similarity	NPC107674
0.7113	Intermediate Similarity	NPC195424
0.7103	Intermediate Similarity	NPC252295
0.71	Intermediate Similarity	NPC474218
0.7091	Intermediate Similarity	NPC472227
0.7091	Intermediate Similarity	NPC472228
0.7091	Intermediate Similarity	NPC164835
0.7091	Intermediate Similarity	NPC255309
0.7091	Intermediate Similarity	NPC228669
0.7091	Intermediate Similarity	NPC471293
0.7087	Intermediate Similarity	NPC469595
0.7087	Intermediate Similarity	NPC212679
0.7087	Intermediate Similarity	NPC220454
0.7087	Intermediate Similarity	NPC44240
0.7083	Intermediate Similarity	NPC4827
0.7075	Intermediate Similarity	NPC58052
0.7075	Intermediate Similarity	NPC111684
0.7071	Intermediate Similarity	NPC470948
0.7059	Intermediate Similarity	NPC294480
0.7059	Intermediate Similarity	NPC477128
0.7053	Intermediate Similarity	NPC92489
0.7049	Intermediate Similarity	NPC96010
0.7049	Intermediate Similarity	NPC317654
0.7048	Intermediate Similarity	NPC471720
0.7048	Intermediate Similarity	NPC294266
0.7041	Intermediate Similarity	NPC201912
0.7041	Intermediate Similarity	NPC232625
0.7041	Intermediate Similarity	NPC38350
0.7037	Intermediate Similarity	NPC470906
0.7037	Intermediate Similarity	NPC476303
0.703	Intermediate Similarity	NPC6979
0.703	Intermediate Similarity	NPC10005
0.703	Intermediate Similarity	NPC55309
0.703	Intermediate Similarity	NPC91525
0.703	Intermediate Similarity	NPC28252
0.703	Intermediate Similarity	NPC329943
0.703	Intermediate Similarity	NPC9892
0.703	Intermediate Similarity	NPC325594
0.7027	Intermediate Similarity	NPC96377
0.7021	Intermediate Similarity	NPC166797
0.7019	Intermediate Similarity	NPC190442
0.7019	Intermediate Similarity	NPC110657
0.7019	Intermediate Similarity	NPC189520
0.7019	Intermediate Similarity	NPC212301
0.7019	Intermediate Similarity	NPC86266
0.7019	Intermediate Similarity	NPC297265
0.701	Intermediate Similarity	NPC471475
0.701	Intermediate Similarity	NPC477371
0.7009	Intermediate Similarity	NPC474164
0.7009	Intermediate Similarity	NPC187159
0.7009	Intermediate Similarity	NPC23680
0.7009	Intermediate Similarity	NPC107243
0.7009	Intermediate Similarity	NPC226986
0.7009	Intermediate Similarity	NPC57416
0.7	Intermediate Similarity	NPC221758
0.7	Intermediate Similarity	NPC214043
0.7	Intermediate Similarity	NPC312660
0.7	Intermediate Similarity	NPC475509
0.7	Intermediate Similarity	NPC85774
0.7	Intermediate Similarity	NPC82902
0.7	Intermediate Similarity	NPC59453
0.6991	Remote Similarity	NPC253645
0.6991	Remote Similarity	NPC147835
0.6991	Remote Similarity	NPC85001
0.6991	Remote Similarity	NPC95920
0.699	Remote Similarity	NPC215029
0.699	Remote Similarity	NPC77168
0.699	Remote Similarity	NPC11611
0.699	Remote Similarity	NPC84271
0.699	Remote Similarity	NPC476733
0.699	Remote Similarity	NPC54689
0.699	Remote Similarity	NPC305039
0.699	Remote Similarity	NPC102414
0.699	Remote Similarity	NPC474679
0.6981	Remote Similarity	NPC69548
0.6981	Remote Similarity	NPC184848
0.6981	Remote Similarity	NPC33473
0.6981	Remote Similarity	NPC279974
0.6972	Remote Similarity	NPC474327
0.697	Remote Similarity	NPC178676
0.697	Remote Similarity	NPC321289
0.697	Remote Similarity	NPC327969
0.697	Remote Similarity	NPC133391
0.697	Remote Similarity	NPC328351
0.697	Remote Similarity	NPC151519
0.697	Remote Similarity	NPC320514
0.697	Remote Similarity	NPC142683
0.697	Remote Similarity	NPC476458
0.697	Remote Similarity	NPC260956
0.697	Remote Similarity	NPC258153
0.6964	Remote Similarity	NPC220974
0.6964	Remote Similarity	NPC59530
0.6961	Remote Similarity	NPC312215
0.6961	Remote Similarity	NPC162107
0.6961	Remote Similarity	NPC46912
0.6952	Remote Similarity	NPC475700
0.6952	Remote Similarity	NPC475657
0.6952	Remote Similarity	NPC66429
0.6952	Remote Similarity	NPC152897
0.6952	Remote Similarity	NPC93027
0.6952	Remote Similarity	NPC477855
0.6952	Remote Similarity	NPC229976
0.6952	Remote Similarity	NPC474185
0.6949	Remote Similarity	NPC470276
0.6944	Remote Similarity	NPC176845
0.6944	Remote Similarity	NPC477813
0.6939	Remote Similarity	NPC267517
0.6939	Remote Similarity	NPC474956
0.6937	Remote Similarity	NPC475239
0.6931	Remote Similarity	NPC329738

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 NPC128698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	589
0.2-0.3	3489
0.3-0.4	3571
0.4-0.5	890
0.5-0.6	343
0.6-0.7	162
0.7-0.8	22
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
0.7745	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6903	Approved
0.7551	Intermediate Similarity	NPD7521	Approved
0.7551	Intermediate Similarity	NPD7334	Approved
0.7551	Intermediate Similarity	NPD6409	Approved
0.7551	Intermediate Similarity	NPD7146	Approved
0.7551	Intermediate Similarity	NPD6684	Approved
0.7551	Intermediate Similarity	NPD5330	Approved
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.74	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5737	Approved
0.74	Intermediate Similarity	NPD6672	Approved
0.7308	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5207	Approved
0.7212	Intermediate Similarity	NPD6001	Approved
0.72	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD5208	Approved
0.7027	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.699	Remote Similarity	NPD6080	Approved
0.699	Remote Similarity	NPD6904	Approved
0.699	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD3667	Approved
0.6944	Remote Similarity	NPD5696	Approved
0.6863	Remote Similarity	NPD3618	Phase 1
0.6857	Remote Similarity	NPD5693	Phase 1
0.6852	Remote Similarity	NPD6083	Phase 2
0.6852	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6832	Remote Similarity	NPD3668	Phase 3
0.6822	Remote Similarity	NPD5695	Phase 3
0.6762	Remote Similarity	NPD5692	Phase 3
0.6729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7900	Approved
0.67	Remote Similarity	NPD857	Phase 3
0.6698	Remote Similarity	NPD6050	Approved
0.6698	Remote Similarity	NPD8034	Phase 2
0.6698	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD6052	Approved
0.6694	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7147	Phase 3
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4221	Approved
0.6634	Remote Similarity	NPD4223	Phase 3
0.6609	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1694	Approved
0.6579	Remote Similarity	NPD5739	Approved
0.6579	Remote Similarity	NPD7128	Approved
0.6579	Remote Similarity	NPD6402	Approved
0.6579	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD7748	Approved
0.6574	Remote Similarity	NPD5707	Approved
0.6552	Remote Similarity	NPD6373	Approved
0.6552	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD5284	Approved
0.6542	Remote Similarity	NPD5281	Approved
0.6542	Remote Similarity	NPD6079	Approved
0.6538	Remote Similarity	NPD5279	Phase 3
0.6526	Remote Similarity	NPD4747	Approved
0.6525	Remote Similarity	NPD7336	Phase 2
0.6525	Remote Similarity	NPD7335	Phase 2
0.6525	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5697	Approved
0.6522	Remote Similarity	NPD5701	Approved
0.6509	Remote Similarity	NPD4753	Phase 2
0.6505	Remote Similarity	NPD4197	Approved
0.6504	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD6909	Approved
0.6481	Remote Similarity	NPD4202	Approved
0.6476	Remote Similarity	NPD3573	Approved
0.6466	Remote Similarity	NPD6899	Approved
0.6466	Remote Similarity	NPD6011	Approved
0.6466	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD4697	Phase 3
0.6442	Remote Similarity	NPD5329	Approved
0.6441	Remote Similarity	NPD6649	Approved
0.6441	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6404	Discontinued
0.6421	Remote Similarity	NPD4137	Phase 3
0.641	Remote Similarity	NPD6013	Approved
0.641	Remote Similarity	NPD6014	Approved
0.641	Remote Similarity	NPD6012	Approved
0.6408	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7515	Phase 2
0.6381	Remote Similarity	NPD4688	Approved
0.6381	Remote Similarity	NPD4689	Approved
0.6381	Remote Similarity	NPD4693	Phase 3
0.6381	Remote Similarity	NPD4690	Approved
0.6381	Remote Similarity	NPD5205	Approved
0.6381	Remote Similarity	NPD4138	Approved
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6364	Remote Similarity	NPD5654	Approved
0.6356	Remote Similarity	NPD7290	Approved
0.6356	Remote Similarity	NPD6883	Approved
0.6356	Remote Similarity	NPD7102	Approved
0.6354	Remote Similarity	NPD4691	Approved
0.6341	Remote Similarity	NPD7519	Approved
0.6341	Remote Similarity	NPD7518	Approved
0.6341	Remote Similarity	NPD7517	Approved
0.6339	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5222	Approved
0.6306	Remote Similarity	NPD5221	Approved
0.6306	Remote Similarity	NPD7732	Phase 3
0.6306	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8130	Phase 1
0.6303	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6847	Approved
0.6303	Remote Similarity	NPD6869	Approved
0.6303	Remote Similarity	NPD6617	Approved
0.6296	Remote Similarity	NPD4096	Approved
0.6289	Remote Similarity	NPD5777	Approved
0.6283	Remote Similarity	NPD7639	Approved
0.6283	Remote Similarity	NPD7640	Approved
0.6273	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7122	Discontinued
0.6263	Remote Similarity	NPD6942	Approved
0.6263	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD5959	Approved
0.624	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6614	Approved
0.6238	Remote Similarity	NPD3617	Approved
0.6231	Remote Similarity	NPD6914	Discontinued
0.6226	Remote Similarity	NPD4694	Approved
0.6226	Remote Similarity	NPD5280	Approved
0.6226	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5690	Phase 2
0.6218	Remote Similarity	NPD6420	Discontinued
0.6202	Remote Similarity	NPD8337	Approved
0.6202	Remote Similarity	NPD8336	Approved
0.62	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7115	Discovery
0.6162	Remote Similarity	NPD5733	Approved
0.6162	Remote Similarity	NPD4687	Approved
0.6162	Remote Similarity	NPD4058	Approved
0.6154	Remote Similarity	NPD7333	Discontinued
0.6142	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD4700	Approved
0.614	Remote Similarity	NPD8418	Phase 2
0.614	Remote Similarity	NPD5286	Approved
0.614	Remote Similarity	NPD5285	Approved
0.614	Remote Similarity	NPD4696	Approved
0.6122	Remote Similarity	NPD5276	Approved
0.6107	Remote Similarity	NPD7751	Phase 1
0.6102	Remote Similarity	NPD6412	Phase 2
0.61	Remote Similarity	NPD3702	Approved
0.6098	Remote Similarity	NPD6274	Approved
0.6098	Remote Similarity	NPD6868	Approved
0.6095	Remote Similarity	NPD4788	Approved
0.6091	Remote Similarity	NPD6411	Approved
0.6087	Remote Similarity	NPD5223	Approved
0.6066	Remote Similarity	NPD7094	Approved
0.6066	Remote Similarity	NPD4632	Approved
0.6066	Remote Similarity	NPD6858	Approved
0.6058	Remote Similarity	NPD4692	Approved
0.6058	Remote Similarity	NPD4139	Approved
0.6048	Remote Similarity	NPD6317	Approved
0.6036	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5224	Approved
0.6034	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD5226	Approved
0.6034	Remote Similarity	NPD4633	Approved
0.6034	Remote Similarity	NPD5225	Approved
0.6029	Remote Similarity	NPD6334	Approved
0.6029	Remote Similarity	NPD6333	Approved
0.6019	Remote Similarity	NPD4195	Approved
0.6018	Remote Similarity	NPD7614	Phase 1
0.6015	Remote Similarity	NPD8449	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD6313	Approved
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4754	Approved
0.5983	Remote Similarity	NPD5174	Approved
0.5983	Remote Similarity	NPD5175	Approved
0.597	Remote Similarity	NPD8450	Suspended
0.5969	Remote Similarity	NPD7492	Approved
0.5968	Remote Similarity	NPD4766	Approved
0.5962	Remote Similarity	NPD7525	Registered
0.5962	Remote Similarity	NPD4695	Discontinued
0.596	Remote Similarity	NPD4243	Approved
0.5952	Remote Similarity	NPD7101	Approved
0.5952	Remote Similarity	NPD7100	Approved
0.5946	Remote Similarity	NPD7637	Suspended
0.5943	Remote Similarity	NPD5362	Discontinued
0.5941	Remote Similarity	NPD8039	Approved
0.5932	Remote Similarity	NPD5141	Approved
0.5926	Remote Similarity	NPD4623	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