NPASS Compound

Structure

CID14339 OpenBabel06191715342D 27 31 0 0 1 0 0 0 0 0999 V2000 -2.2707 1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8753 -3.8455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3481 1.6377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6429 0.6888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2010 -2.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6362 -2.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0381 -1.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4726 -1.4191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1449 -0.6415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0381 -2.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9178 -1.4633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6362 -1.4289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9656 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0065 -1.7860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2010 -0.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8924 -0.4970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3585 -0.1301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7215 -0.2481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9614 0.1010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3545 -0.7820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4181 -1.0191 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 -2.5595 0.8155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9280 1.7754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8753 -2.8789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6468 0.7184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5468 -0.0339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 9 27 1 0 0 0 0 10 25 1 0 0 0 0 11 9 1 1 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 8 1 1 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 13 1 6 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 1 0 0 0 18 20 1 1 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 8 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.17
Volume:	364.456
LogP:	2.287
LogD:	2.209
LogS:	-4.658
# Rotatable Bonds:	3
TPSA:	80.59
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.869
Synthetic Accessibility Score:	6.368
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.011
MDCK Permeability:	1.0605235729599372e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.873
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.69
Plasma Protein Binding (PPB):	75.30457305908203%
Volume Distribution (VD):	1.025
Pgp-substrate:	16.02664566040039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.462
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	10.531
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.879
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.19
Carcinogencity:	0.901
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC14339

Natural Product ID:	NPC14339
*Common Name:**	VXQDOSKGLXGDFW-RQYAOBBUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VXQDOSKGLXGDFW-RQYAOBBUSA-N
Standard InCHI:	InChI=1S/C20H24N2O5/c1-4-13-16-11-9-27-18(17(16)23)20(8-14(11)21-13)12-6-5-10(25-2)7-15(12)22(26-3)19(20)24/h5-7,11,14,16-18,23H,4,8-9H2,1-3H3/t11-,14+,16-,17-,18-,20+/m1/s1
SMILES:	CCC1=N[C@H]2C[C@]3(c4ccc(cc4N(C3=O)OC)OC)[C@H]3[C@@H]([C@@H]1[C@@H]2CO3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525557
PubChem CID:	12070888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655795]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12651	Gelsemium sempervirens	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	>	100000.0	nM	PMID[519126]

☑ 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 NPC14339 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	297
0.1-0.2	1486
0.2-0.3	6041
0.3-0.4	11436
0.4-0.5	14472
0.5-0.6	7833
0.6-0.7	1068
0.7-0.8	51
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8677	High Similarity	NPC243626
0.8673	High Similarity	NPC477160
0.8579	High Similarity	NPC230313
0.8571	High Similarity	NPC473004
0.8495	Intermediate Similarity	NPC245741
0.8368	Intermediate Similarity	NPC473008
0.8315	Intermediate Similarity	NPC13367
0.8307	Intermediate Similarity	NPC282092
0.8158	Intermediate Similarity	NPC473007
0.815	Intermediate Similarity	NPC477161
0.8122	Intermediate Similarity	NPC143457
0.802	Intermediate Similarity	NPC475559
0.802	Intermediate Similarity	NPC302548
0.8	Intermediate Similarity	NPC204970
0.7961	Intermediate Similarity	NPC473006
0.7806	Intermediate Similarity	NPC174629
0.7734	Intermediate Similarity	NPC473005
0.7723	Intermediate Similarity	NPC67904
0.768	Intermediate Similarity	NPC477159
0.7656	Intermediate Similarity	NPC10732
0.7624	Intermediate Similarity	NPC100863
0.7577	Intermediate Similarity	NPC39822
0.7571	Intermediate Similarity	NPC159815
0.757	Intermediate Similarity	NPC10653
0.757	Intermediate Similarity	NPC318525
0.7538	Intermediate Similarity	NPC473569
0.7488	Intermediate Similarity	NPC127996
0.7487	Intermediate Similarity	NPC284706
0.7473	Intermediate Similarity	NPC29285
0.7463	Intermediate Similarity	NPC127178
0.745	Intermediate Similarity	NPC474059
0.7426	Intermediate Similarity	NPC203972
0.7413	Intermediate Similarity	NPC28510
0.7407	Intermediate Similarity	NPC286871
0.7391	Intermediate Similarity	NPC474077
0.7379	Intermediate Similarity	NPC138830
0.7361	Intermediate Similarity	NPC37957
0.7352	Intermediate Similarity	NPC122886
0.7333	Intermediate Similarity	NPC184680
0.7311	Intermediate Similarity	NPC476651
0.7302	Intermediate Similarity	NPC470001
0.7302	Intermediate Similarity	NPC470002
0.7301	Intermediate Similarity	NPC470784
0.7301	Intermediate Similarity	NPC470785
0.7301	Intermediate Similarity	NPC474183
0.7281	Intermediate Similarity	NPC153923
0.7281	Intermediate Similarity	NPC288110
0.7252	Intermediate Similarity	NPC74216
0.7243	Intermediate Similarity	NPC470481
0.7243	Intermediate Similarity	NPC470482
0.724	Intermediate Similarity	NPC266994
0.7238	Intermediate Similarity	NPC87714
0.7225	Intermediate Similarity	NPC176983
0.7215	Intermediate Similarity	NPC46259
0.7207	Intermediate Similarity	NPC470480
0.72	Intermediate Similarity	NPC473105
0.7183	Intermediate Similarity	NPC168250
0.7182	Intermediate Similarity	NPC71539
0.7182	Intermediate Similarity	NPC250960
0.7157	Intermediate Similarity	NPC129624
0.7156	Intermediate Similarity	NPC77777
0.7143	Intermediate Similarity	NPC470821
0.7143	Intermediate Similarity	NPC234772
0.7136	Intermediate Similarity	NPC205926
0.713	Intermediate Similarity	NPC473458
0.7123	Intermediate Similarity	NPC108826
0.712	Intermediate Similarity	NPC310403
0.712	Intermediate Similarity	NPC97380
0.712	Intermediate Similarity	NPC263709
0.712	Intermediate Similarity	NPC63210
0.712	Intermediate Similarity	NPC243673
0.712	Intermediate Similarity	NPC148468
0.7116	Intermediate Similarity	NPC82541
0.711	Intermediate Similarity	NPC126556
0.7109	Intermediate Similarity	NPC41216
0.7103	Intermediate Similarity	NPC471561
0.7103	Intermediate Similarity	NPC469589
0.7083	Intermediate Similarity	NPC119722
0.7078	Intermediate Similarity	NPC303658
0.7078	Intermediate Similarity	NPC473041
0.7073	Intermediate Similarity	NPC22476
0.707	Intermediate Similarity	NPC269449
0.7067	Intermediate Similarity	NPC161804
0.7067	Intermediate Similarity	NPC477397
0.7067	Intermediate Similarity	NPC272706
0.7062	Intermediate Similarity	NPC470069
0.7062	Intermediate Similarity	NPC52059
0.7051	Intermediate Similarity	NPC217903
0.7045	Intermediate Similarity	NPC222046
0.7044	Intermediate Similarity	NPC262725
0.7028	Intermediate Similarity	NPC473460
0.7027	Intermediate Similarity	NPC148124
0.7024	Intermediate Similarity	NPC283207
0.7018	Intermediate Similarity	NPC189661
0.7014	Intermediate Similarity	NPC128115
0.7009	Intermediate Similarity	NPC478075
0.7005	Intermediate Similarity	NPC264176
0.7005	Intermediate Similarity	NPC116178
0.6995	Remote Similarity	NPC475147
0.6995	Remote Similarity	NPC163829
0.6987	Remote Similarity	NPC291173
0.6982	Remote Similarity	NPC99724
0.6982	Remote Similarity	NPC128476
0.6979	Remote Similarity	NPC153694
0.6979	Remote Similarity	NPC211525
0.6978	Remote Similarity	NPC471513
0.6977	Remote Similarity	NPC475910
0.6977	Remote Similarity	NPC90185
0.6977	Remote Similarity	NPC317709
0.6977	Remote Similarity	NPC329329
0.6976	Remote Similarity	NPC217294
0.6974	Remote Similarity	NPC70172
0.6972	Remote Similarity	NPC469592
0.6972	Remote Similarity	NPC471080
0.697	Remote Similarity	NPC276993
0.697	Remote Similarity	NPC210415
0.697	Remote Similarity	NPC293255
0.697	Remote Similarity	NPC21752
0.697	Remote Similarity	NPC475816
0.697	Remote Similarity	NPC181138
0.697	Remote Similarity	NPC298851
0.6964	Remote Similarity	NPC97746
0.6963	Remote Similarity	NPC158551
0.6963	Remote Similarity	NPC161827
0.6955	Remote Similarity	NPC313327
0.6955	Remote Similarity	NPC305984
0.6953	Remote Similarity	NPC188400
0.6948	Remote Similarity	NPC207971
0.6947	Remote Similarity	NPC194740
0.6944	Remote Similarity	NPC475133
0.6933	Remote Similarity	NPC476436
0.693	Remote Similarity	NPC474192
0.693	Remote Similarity	NPC475720
0.6927	Remote Similarity	NPC21425
0.6927	Remote Similarity	NPC472098
0.6923	Remote Similarity	NPC469594
0.6916	Remote Similarity	NPC268077
0.6908	Remote Similarity	NPC203628
0.6903	Remote Similarity	NPC248903
0.6901	Remote Similarity	NPC52801
0.6895	Remote Similarity	NPC321166
0.6893	Remote Similarity	NPC477186
0.6892	Remote Similarity	NPC298436
0.6889	Remote Similarity	NPC19175
0.6889	Remote Similarity	NPC231924
0.6872	Remote Similarity	NPC71124
0.686	Remote Similarity	NPC105055
0.686	Remote Similarity	NPC22689
0.6858	Remote Similarity	NPC26928
0.6854	Remote Similarity	NPC232600
0.6853	Remote Similarity	NPC278887
0.6852	Remote Similarity	NPC198160
0.6847	Remote Similarity	NPC270301
0.6847	Remote Similarity	NPC28368
0.6847	Remote Similarity	NPC475962
0.6842	Remote Similarity	NPC79293
0.6842	Remote Similarity	NPC279401
0.6842	Remote Similarity	NPC470485
0.6839	Remote Similarity	NPC10875
0.6839	Remote Similarity	NPC10730
0.6838	Remote Similarity	NPC477395
0.6833	Remote Similarity	NPC330009
0.6825	Remote Similarity	NPC472191
0.6822	Remote Similarity	NPC311357
0.6816	Remote Similarity	NPC168153
0.6816	Remote Similarity	NPC219397
0.6814	Remote Similarity	NPC98197
0.6806	Remote Similarity	NPC195787
0.6806	Remote Similarity	NPC246140
0.6804	Remote Similarity	NPC471532
0.6802	Remote Similarity	NPC195636
0.6802	Remote Similarity	NPC472106
0.6798	Remote Similarity	NPC311906
0.6786	Remote Similarity	NPC472101
0.6786	Remote Similarity	NPC472120
0.6786	Remote Similarity	NPC67080
0.6786	Remote Similarity	NPC472117
0.6786	Remote Similarity	NPC472121
0.6783	Remote Similarity	NPC476429
0.678	Remote Similarity	NPC477393
0.6777	Remote Similarity	NPC303214
0.6771	Remote Similarity	NPC219383
0.6771	Remote Similarity	NPC96321
0.6759	Remote Similarity	NPC473422
0.6759	Remote Similarity	NPC470484
0.6758	Remote Similarity	NPC269367
0.6757	Remote Similarity	NPC471531
0.6757	Remote Similarity	NPC148183
0.6757	Remote Similarity	NPC152768
0.6756	Remote Similarity	NPC329830
0.6752	Remote Similarity	NPC49583
0.6751	Remote Similarity	NPC58209
0.675	Remote Similarity	NPC189079
0.6749	Remote Similarity	NPC274002
0.6749	Remote Similarity	NPC126515
0.6749	Remote Similarity	NPC472331
0.6748	Remote Similarity	NPC102760
0.6746	Remote Similarity	NPC470483
0.6744	Remote Similarity	NPC295898
0.6743	Remote Similarity	NPC207873

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 NPC14339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	583
0.2-0.3	850
0.3-0.4	1682
0.4-0.5	3027
0.5-0.6	2438
0.6-0.7	372
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7452	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6457	Approved
0.7143	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5617	Suspended
0.7037	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6238	Discontinued
0.7014	Intermediate Similarity	NPD3437	Discontinued
0.699	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3153	Approved
0.6961	Remote Similarity	NPD3154	Approved
0.6941	Remote Similarity	NPD7559	Phase 2
0.6923	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7820	Phase 3
0.692	Remote Similarity	NPD3912	Discontinued
0.69	Remote Similarity	NPD4373	Phase 2
0.6884	Remote Similarity	NPD3003	Approved
0.6869	Remote Similarity	NPD5186	Approved
0.6869	Remote Similarity	NPD5183	Approved
0.6858	Remote Similarity	NPD7426	Phase 1
0.6847	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6874	Approved
0.6838	Remote Similarity	NPD6517	Phase 3
0.6834	Remote Similarity	NPD2216	Approved
0.6834	Remote Similarity	NPD2215	Approved
0.6833	Remote Similarity	NPD5025	Approved
0.6824	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8016	Phase 3
0.6823	Remote Similarity	NPD5811	Approved
0.6822	Remote Similarity	NPD8359	Phase 2
0.6812	Remote Similarity	NPD6962	Phase 2
0.6808	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD683	Approved
0.6782	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2843	Phase 2
0.6779	Remote Similarity	NPD2845	Phase 2
0.6774	Remote Similarity	NPD6296	Discontinued
0.6769	Remote Similarity	NPD4952	Phase 3
0.6769	Remote Similarity	NPD4981	Phase 2
0.6768	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1768	Approved
0.6758	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3983	Phase 3
0.6734	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8460	Approved
0.6732	Remote Similarity	NPD8459	Approved
0.6726	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4796	Discontinued
0.6706	Remote Similarity	NPD8467	Approved
0.6706	Remote Similarity	NPD8466	Approved
0.6706	Remote Similarity	NPD8465	Approved
0.6701	Remote Similarity	NPD1743	Approved
0.6701	Remote Similarity	NPD1742	Approved
0.6701	Remote Similarity	NPD19	Approved
0.6699	Remote Similarity	NPD7281	Phase 3
0.6699	Remote Similarity	NPD7280	Phase 3
0.6698	Remote Similarity	NPD3416	Discontinued
0.6698	Remote Similarity	NPD5512	Phase 3
0.6695	Remote Similarity	NPD6716	Phase 1
0.6682	Remote Similarity	NPD4539	Phase 1
0.6681	Remote Similarity	NPD7556	Discontinued
0.6681	Remote Similarity	NPD7805	Phase 3
0.6667	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8364	Approved
0.6667	Remote Similarity	NPD8363	Approved
0.6667	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8255	Phase 2
0.6653	Remote Similarity	NPD6790	Phase 1
0.6652	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6519	Phase 2
0.665	Remote Similarity	NPD5967	Approved
0.664	Remote Similarity	NPD8429	Approved
0.664	Remote Similarity	NPD8428	Approved
0.664	Remote Similarity	NPD8427	Approved
0.6637	Remote Similarity	NPD5903	Approved
0.6637	Remote Similarity	NPD5902	Approved
0.6635	Remote Similarity	NPD5937	Approved
0.6634	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5632	Approved
0.6622	Remote Similarity	NPD7605	Discovery
0.662	Remote Similarity	NPD5582	Discontinued
0.6618	Remote Similarity	NPD5313	Approved
0.6618	Remote Similarity	NPD5312	Approved
0.6614	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4328	Approved
0.6609	Remote Similarity	NPD6723	Discontinued
0.6606	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD8426	Approved
0.6602	Remote Similarity	NPD8425	Approved
0.6601	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5519	Discontinued
0.6592	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2916	Discontinued
0.6589	Remote Similarity	NPD4604	Approved
0.6589	Remote Similarity	NPD4605	Approved
0.6589	Remote Similarity	NPD5515	Phase 2
0.6588	Remote Similarity	NPD5641	Discontinued
0.6585	Remote Similarity	NPD7479	Phase 2
0.6585	Remote Similarity	NPD5557	Phase 1
0.6584	Remote Similarity	NPD4083	Discontinued
0.6571	Remote Similarity	NPD2792	Approved
0.6567	Remote Similarity	NPD4885	Approved
0.6567	Remote Similarity	NPD7797	Approved
0.6567	Remote Similarity	NPD7796	Approved
0.6565	Remote Similarity	NPD7186	Phase 3
0.6562	Remote Similarity	NPD4897	Phase 2
0.6562	Remote Similarity	NPD5293	Phase 2
0.6558	Remote Similarity	NPD4668	Phase 2
0.6557	Remote Similarity	NPD3634	Approved
0.6557	Remote Similarity	NPD3633	Approved
0.6553	Remote Similarity	NPD6878	Phase 2
0.6553	Remote Similarity	NPD6879	Phase 2
0.6552	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7453	Approved
0.6545	Remote Similarity	NPD7956	Approved
0.6545	Remote Similarity	NPD7955	Approved
0.6545	Remote Similarity	NPD7452	Approved
0.6545	Remote Similarity	NPD1392	Approved
0.6542	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7630	Phase 3
0.654	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7628	Phase 3
0.6537	Remote Similarity	NPD5600	Discontinued
0.6537	Remote Similarity	NPD3793	Phase 3
0.6537	Remote Similarity	NPD3259	Approved
0.6529	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4466	Phase 1
0.6522	Remote Similarity	NPD4203	Approved
0.6522	Remote Similarity	NPD3037	Phase 1
0.6522	Remote Similarity	NPD4204	Approved
0.652	Remote Similarity	NPD3258	Approved
0.6517	Remote Similarity	NPD5823	Approved
0.6516	Remote Similarity	NPD5658	Approved
0.6516	Remote Similarity	NPD4154	Approved
0.6515	Remote Similarity	NPD7599	Phase 2
0.6514	Remote Similarity	NPD7316	Discontinued
0.6513	Remote Similarity	NPD7417	Discontinued
0.6509	Remote Similarity	NPD5014	Discontinued
0.6509	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5601	Phase 2
0.65	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4418	Discontinued
0.6493	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3909	Discontinued
0.6488	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3591	Approved
0.6486	Remote Similarity	NPD3592	Approved
0.6485	Remote Similarity	NPD2821	Approved
0.6484	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3802	Phase 3
0.6484	Remote Similarity	NPD6669	Phase 2
0.6481	Remote Similarity	NPD5071	Phase 2
0.648	Remote Similarity	NPD7803	Approved
0.648	Remote Similarity	NPD6357	Discontinued
0.6479	Remote Similarity	NPD5587	Approved
0.6474	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7560	Approved
0.6471	Remote Similarity	NPD7222	Phase 2
0.6468	Remote Similarity	NPD7558	Phase 2
0.6466	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4258	Approved
0.6462	Remote Similarity	NPD1670	Discontinued
0.6462	Remote Similarity	NPD4259	Approved
0.6457	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4846	Phase 2
0.6456	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1294	Discontinued
0.6453	Remote Similarity	NPD7315	Approved
0.6452	Remote Similarity	NPD7565	Approved
0.6449	Remote Similarity	NPD3631	Phase 3
0.6449	Remote Similarity	NPD7125	Discontinued
0.6447	Remote Similarity	NPD7194	Discontinued
0.6445	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8027	Approved
0.6438	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2904	Discontinued
0.6435	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5772	Approved
0.6432	Remote Similarity	NPD5773	Approved
0.6429	Remote Similarity	NPD4003	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