NPASS Compound

Structure

NPC473007 OpenBabel07101718332D 25 29 0 0 1 0 0 0 0 0999 V2000 1.8964 -0.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0606 -1.2952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0175 -0.7156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1302 0.5141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1310 0.5533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0622 -1.2166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4540 -0.7270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 0.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1526 -0.0366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 0.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1649 -0.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5958 -0.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0199 -0.2531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0199 0.4171 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5973 -0.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0629 -1.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4540 0.8910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1242 -0.7270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -0.2531 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5293 -2.0231 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 -0.5507 -1.6948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5950 -0.4102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3336 0.0544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 3 11 2 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 12 24 1 0 0 0 0 13 7 1 6 0 0 0 13 14 1 0 0 0 0 14 10 1 1 0 0 0 14 17 1 0 0 0 0 15 16 2 0 0 0 0 16 21 1 0 0 0 0 17 8 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	346.876
LogP:	2.692
LogD:	2.689
LogS:	-3.696
# Rotatable Bonds:	2
TPSA:	64.79
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	5.797
Fsp3:	0.55
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:	-5.08
MDCK Permeability:	9.637300536269322e-06
Pgp-inhibitor:	0.051
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	69.2330551147461%
Volume Distribution (VD):	1.48
Pgp-substrate:	25.34725570678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.252
CYP2C19-inhibitor:	0.43
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	10.624
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.528
Drug-inuced Liver Injury (DILI):	0.402
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.559
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC473007

Natural Product ID:	NPC473007
*Common Name:**	GJTBZLZKFLDAQJ-WSIGHSHASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GJTBZLZKFLDAQJ-WSIGHSHASA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-3-11-9-22-17-8-20(19(22)23,18-7-13(11)14(17)10-25-18)15-5-4-12(24-2)6-16(15)21/h3-6,13-14,17-18H,7-10,21H2,1-2H3/b11-3+/t13-,14-,17-,18+,20-/m0/s1
SMILES:	C/C=C/1CN2[C@@H]3[C@@H]4[C@H]1C[C@H]([C@](C2=O)(C3)c1ccc(cc1N)OC)OC4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597663
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines [CHEMONTID:0002336] Phenylpyrrolidines

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[490593]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[490593]

☑ 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 NPC473007 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	336
0.1-0.2	1564
0.2-0.3	5834
0.3-0.4	11695
0.4-0.5	15526
0.5-0.6	6630
0.6-0.7	1007
0.7-0.8	93
0.8-0.85	5
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC473008
0.931	High Similarity	NPC230313
0.9195	High Similarity	NPC473004
0.8983	High Similarity	NPC243626
0.8846	High Similarity	NPC473005
0.8663	High Similarity	NPC477160
0.8602	High Similarity	NPC477161
0.8533	High Similarity	NPC67904
0.8525	High Similarity	NPC100863
0.8385	Intermediate Similarity	NPC473006
0.8242	Intermediate Similarity	NPC473569
0.8158	Intermediate Similarity	NPC14339
0.8144	Intermediate Similarity	NPC10732
0.8138	Intermediate Similarity	NPC138830
0.8054	Intermediate Similarity	NPC204970
0.8051	Intermediate Similarity	NPC159815
0.8012	Intermediate Similarity	NPC29285
0.794	Intermediate Similarity	NPC77777
0.7931	Intermediate Similarity	NPC176983
0.7849	Intermediate Similarity	NPC174629
0.7807	Intermediate Similarity	NPC22476
0.7772	Intermediate Similarity	NPC318525
0.7772	Intermediate Similarity	NPC10653
0.7754	Intermediate Similarity	NPC474059
0.7727	Intermediate Similarity	NPC286871
0.7647	Intermediate Similarity	NPC21425
0.7641	Intermediate Similarity	NPC41216
0.7577	Intermediate Similarity	NPC127178
0.755	Intermediate Similarity	NPC82541
0.7525	Intermediate Similarity	NPC478075
0.7513	Intermediate Similarity	NPC87714
0.7452	Intermediate Similarity	NPC122886
0.7435	Intermediate Similarity	NPC28510
0.7433	Intermediate Similarity	NPC477159
0.7432	Intermediate Similarity	NPC96901
0.7424	Intermediate Similarity	NPC475147
0.7419	Intermediate Similarity	NPC39822
0.7415	Intermediate Similarity	NPC473041
0.7379	Intermediate Similarity	NPC37957
0.7366	Intermediate Similarity	NPC305984
0.7363	Intermediate Similarity	NPC475133
0.7358	Intermediate Similarity	NPC203972
0.7354	Intermediate Similarity	NPC102760
0.7353	Intermediate Similarity	NPC189661
0.7344	Intermediate Similarity	NPC203628
0.734	Intermediate Similarity	NPC127996
0.7337	Intermediate Similarity	NPC251212
0.7337	Intermediate Similarity	NPC139085
0.7337	Intermediate Similarity	NPC214626
0.7308	Intermediate Similarity	NPC279527
0.7308	Intermediate Similarity	NPC214960
0.7296	Intermediate Similarity	NPC71124
0.7292	Intermediate Similarity	NPC105055
0.7292	Intermediate Similarity	NPC22689
0.7286	Intermediate Similarity	NPC473460
0.7286	Intermediate Similarity	NPC207971
0.7282	Intermediate Similarity	NPC195636
0.7282	Intermediate Similarity	NPC126556
0.7278	Intermediate Similarity	NPC143457
0.7264	Intermediate Similarity	NPC74216
0.7263	Intermediate Similarity	NPC113946
0.7251	Intermediate Similarity	NPC266994
0.725	Intermediate Similarity	NPC268077
0.7249	Intermediate Similarity	NPC98197
0.7245	Intermediate Similarity	NPC272706
0.7241	Intermediate Similarity	NPC269449
0.7236	Intermediate Similarity	NPC474077
0.7222	Intermediate Similarity	NPC133817
0.7222	Intermediate Similarity	NPC476443
0.7222	Intermediate Similarity	NPC291173
0.7212	Intermediate Similarity	NPC153923
0.7209	Intermediate Similarity	NPC473105
0.7204	Intermediate Similarity	NPC231924
0.7202	Intermediate Similarity	NPC45389
0.7202	Intermediate Similarity	NPC283207
0.7194	Intermediate Similarity	NPC303214
0.719	Intermediate Similarity	NPC250960
0.719	Intermediate Similarity	NPC71539
0.7189	Intermediate Similarity	NPC184680
0.7186	Intermediate Similarity	NPC232600
0.7183	Intermediate Similarity	NPC311906
0.7182	Intermediate Similarity	NPC309531
0.7182	Intermediate Similarity	NPC472102
0.7178	Intermediate Similarity	NPC198160
0.7177	Intermediate Similarity	NPC476069
0.7171	Intermediate Similarity	NPC264176
0.7171	Intermediate Similarity	NPC470481
0.7171	Intermediate Similarity	NPC470482
0.7171	Intermediate Similarity	NPC119722
0.7158	Intermediate Similarity	NPC472106
0.7158	Intermediate Similarity	NPC299582
0.7157	Intermediate Similarity	NPC161804
0.7157	Intermediate Similarity	NPC476651
0.7156	Intermediate Similarity	NPC470784
0.7156	Intermediate Similarity	NPC470785
0.7151	Intermediate Similarity	NPC161827
0.715	Intermediate Similarity	NPC470001
0.715	Intermediate Similarity	NPC470002
0.7143	Intermediate Similarity	NPC205926
0.7143	Intermediate Similarity	NPC46259
0.7143	Intermediate Similarity	NPC472120
0.7143	Intermediate Similarity	NPC472101
0.7143	Intermediate Similarity	NPC128476
0.7136	Intermediate Similarity	NPC470480
0.7129	Intermediate Similarity	NPC219397
0.7129	Intermediate Similarity	NPC288110
0.7128	Intermediate Similarity	NPC260075
0.7115	Intermediate Similarity	NPC313327
0.7105	Intermediate Similarity	NPC28368
0.7092	Intermediate Similarity	NPC254957
0.7092	Intermediate Similarity	NPC470485
0.7089	Intermediate Similarity	NPC476436
0.7085	Intermediate Similarity	NPC5374
0.7081	Intermediate Similarity	NPC96321
0.7077	Intermediate Similarity	NPC1820
0.7068	Intermediate Similarity	NPC314659
0.7067	Intermediate Similarity	NPC148183
0.7067	Intermediate Similarity	NPC234772
0.7067	Intermediate Similarity	NPC152768
0.7062	Intermediate Similarity	NPC217294
0.7059	Intermediate Similarity	NPC475910
0.7053	Intermediate Similarity	NPC70092
0.7053	Intermediate Similarity	NPC222524
0.705	Intermediate Similarity	NPC329747
0.7049	Intermediate Similarity	NPC472121
0.7049	Intermediate Similarity	NPC472117
0.7044	Intermediate Similarity	NPC246140
0.7044	Intermediate Similarity	NPC195787
0.7042	Intermediate Similarity	NPC21638
0.7042	Intermediate Similarity	NPC19175
0.7033	Intermediate Similarity	NPC97380
0.7033	Intermediate Similarity	NPC243673
0.7033	Intermediate Similarity	NPC148468
0.7033	Intermediate Similarity	NPC63210
0.7033	Intermediate Similarity	NPC263709
0.7033	Intermediate Similarity	NPC310403
0.7024	Intermediate Similarity	NPC168250
0.7021	Intermediate Similarity	NPC13367
0.7016	Intermediate Similarity	NPC197335
0.7005	Intermediate Similarity	NPC116178
0.7	Intermediate Similarity	NPC303658
0.6995	Remote Similarity	NPC473422
0.6991	Remote Similarity	NPC470821
0.699	Remote Similarity	NPC471304
0.699	Remote Similarity	NPC470483
0.6974	Remote Similarity	NPC477259
0.6974	Remote Similarity	NPC284706
0.6974	Remote Similarity	NPC169387
0.6974	Remote Similarity	NPC477186
0.6973	Remote Similarity	NPC52059
0.6973	Remote Similarity	NPC470069
0.6973	Remote Similarity	NPC70172
0.6971	Remote Similarity	NPC321166
0.6971	Remote Similarity	NPC217903
0.6968	Remote Similarity	NPC210415
0.6968	Remote Similarity	NPC475816
0.6968	Remote Similarity	NPC298851
0.6968	Remote Similarity	NPC276993
0.6968	Remote Similarity	NPC181138
0.6968	Remote Similarity	NPC293255
0.6968	Remote Similarity	NPC21752
0.6968	Remote Similarity	NPC73280
0.6966	Remote Similarity	NPC242000
0.6963	Remote Similarity	NPC115588
0.6959	Remote Similarity	NPC116007
0.695	Remote Similarity	NPC234933
0.6939	Remote Similarity	NPC5630
0.6927	Remote Similarity	NPC476429
0.6923	Remote Similarity	NPC474183
0.6923	Remote Similarity	NPC472098
0.6915	Remote Similarity	NPC284842
0.6915	Remote Similarity	NPC241263
0.6915	Remote Similarity	NPC471648
0.6912	Remote Similarity	NPC470484
0.6909	Remote Similarity	NPC154922
0.6905	Remote Similarity	NPC330009
0.6898	Remote Similarity	NPC473458
0.6893	Remote Similarity	NPC317709
0.6893	Remote Similarity	NPC329329
0.6885	Remote Similarity	NPC78733
0.6885	Remote Similarity	NPC153694
0.6885	Remote Similarity	NPC211525
0.6882	Remote Similarity	NPC24954
0.6879	Remote Similarity	NPC106606
0.6878	Remote Similarity	NPC476425
0.6875	Remote Similarity	NPC308197
0.6869	Remote Similarity	NPC206109
0.6869	Remote Similarity	NPC148124
0.6869	Remote Similarity	NPC114039
0.6866	Remote Similarity	NPC471762
0.6866	Remote Similarity	NPC112937
0.6862	Remote Similarity	NPC469915
0.686	Remote Similarity	NPC471561
0.6854	Remote Similarity	NPC472099
0.685	Remote Similarity	NPC477258
0.6849	Remote Similarity	NPC139373
0.6849	Remote Similarity	NPC475720
0.6849	Remote Similarity	NPC474192
0.6848	Remote Similarity	NPC147091
0.6848	Remote Similarity	NPC301163

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 NPC473007 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	616
0.2-0.3	787
0.3-0.4	1677
0.4-0.5	2950
0.5-0.6	2502
0.6-0.7	395
0.7-0.8	12
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
0.7809	Intermediate Similarity	NPD5183	Approved
0.7809	Intermediate Similarity	NPD5186	Approved
0.7733	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD6238	Discontinued
0.7584	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6457	Approved
0.7447	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4166	Phase 2
0.7405	Intermediate Similarity	NPD5313	Approved
0.7405	Intermediate Similarity	NPD5312	Approved
0.733	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3437	Discontinued
0.7166	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2246	Approved
0.7151	Intermediate Similarity	NPD2248	Approved
0.7129	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5600	Discontinued
0.7127	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5071	Phase 2
0.7114	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1307	Phase 2
0.7104	Intermediate Similarity	NPD1309	Phase 2
0.7095	Intermediate Similarity	NPD6357	Discontinued
0.709	Intermediate Similarity	NPD7479	Phase 2
0.7088	Intermediate Similarity	NPD5967	Approved
0.7081	Intermediate Similarity	NPD6107	Approved
0.7081	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3639	Approved
0.7079	Intermediate Similarity	NPD6644	Discontinued
0.7079	Intermediate Similarity	NPD3640	Phase 3
0.7079	Intermediate Similarity	NPD3641	Approved
0.7075	Intermediate Similarity	NPD3912	Discontinued
0.7068	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7626	Approved
0.7065	Intermediate Similarity	NPD7627	Approved
0.7059	Intermediate Similarity	NPD8027	Approved
0.7037	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5293	Phase 2
0.699	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3511	Discontinued
0.6963	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3591	Approved
0.6942	Remote Similarity	NPD3592	Approved
0.6931	Remote Similarity	NPD6321	Discontinued
0.6927	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7110	Phase 1
0.6912	Remote Similarity	NPD4981	Phase 2
0.6912	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6851	Approved
0.6907	Remote Similarity	NPD6853	Approved
0.6901	Remote Similarity	NPD5185	Approved
0.6901	Remote Similarity	NPD5184	Approved
0.6901	Remote Similarity	NPD5182	Approved
0.6898	Remote Similarity	NPD2249	Approved
0.6898	Remote Similarity	NPD2247	Approved
0.6889	Remote Similarity	NPD1670	Discontinued
0.6888	Remote Similarity	NPD3349	Phase 2
0.6885	Remote Similarity	NPD1769	Discontinued
0.6881	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD743	Approved
0.6875	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6297	Approved
0.6868	Remote Similarity	NPD5617	Suspended
0.6859	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7559	Phase 2
0.6856	Remote Similarity	NPD7281	Phase 3
0.6856	Remote Similarity	NPD7280	Phase 3
0.6845	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6037	Discontinued
0.6845	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD3631	Phase 3
0.6825	Remote Similarity	NPD5025	Approved
0.6825	Remote Similarity	NPD5561	Approved
0.6825	Remote Similarity	NPD5562	Approved
0.6816	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4154	Approved
0.6809	Remote Similarity	NPD2680	Approved
0.6809	Remote Similarity	NPD2681	Approved
0.6806	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7248	Discontinued
0.6788	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6879	Phase 2
0.6788	Remote Similarity	NPD6878	Phase 2
0.6786	Remote Similarity	NPD3154	Approved
0.6786	Remote Similarity	NPD3153	Approved
0.6784	Remote Similarity	NPD3479	Discontinued
0.6776	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3793	Phase 3
0.6759	Remote Similarity	NPD7820	Phase 3
0.6757	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5823	Approved
0.6755	Remote Similarity	NPD2904	Discontinued
0.675	Remote Similarity	NPD4539	Phase 1
0.6748	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6250	Discontinued
0.6744	Remote Similarity	NPD7805	Phase 3
0.6739	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD2216	Approved
0.6737	Remote Similarity	NPD2215	Approved
0.6737	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6618	Phase 2
0.6734	Remote Similarity	NPD5994	Discontinued
0.6734	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5515	Phase 2
0.6732	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3983	Phase 3
0.672	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7126	Discontinued
0.6719	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7291	Discontinued
0.6717	Remote Similarity	NPD8025	Phase 2
0.6711	Remote Similarity	NPD6790	Phase 1
0.6703	Remote Similarity	NPD6031	Approved
0.6703	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6030	Approved
0.6702	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4796	Discontinued
0.6702	Remote Similarity	NPD5997	Discontinued
0.67	Remote Similarity	NPD5937	Approved
0.6697	Remote Similarity	NPD4885	Approved
0.6685	Remote Similarity	NPD6876	Approved
0.6685	Remote Similarity	NPD6875	Approved
0.6684	Remote Similarity	NPD19	Approved
0.6684	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2971	Approved
0.6684	Remote Similarity	NPD2968	Approved
0.6684	Remote Similarity	NPD1742	Approved
0.6684	Remote Similarity	NPD1743	Approved
0.6683	Remote Similarity	NPD5114	Approved
0.6683	Remote Similarity	NPD4258	Approved
0.6683	Remote Similarity	NPD5112	Approved
0.6683	Remote Similarity	NPD5113	Approved
0.6683	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4259	Approved
0.6667	Remote Similarity	NPD3037	Phase 1
0.6667	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8359	Phase 2
0.6667	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4465	Phase 2
0.6667	Remote Similarity	NPD4467	Phase 2
0.6667	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6874	Approved
0.6651	Remote Similarity	NPD5658	Approved
0.665	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4772	Phase 2
0.6649	Remote Similarity	NPD4773	Phase 2
0.6648	Remote Similarity	NPD3170	Approved
0.6635	Remote Similarity	NPD5601	Phase 2
0.6635	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5811	Approved
0.663	Remote Similarity	NPD7598	Phase 2
0.663	Remote Similarity	NPD3124	Discontinued
0.6629	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7426	Phase 1
0.662	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD4710	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7298	Approved
0.6612	Remote Similarity	NPD7427	Discontinued
0.6601	Remote Similarity	NPD3964	Approved
0.6601	Remote Similarity	NPD5582	Discontinued
0.66	Remote Similarity	NPD2845	Phase 2
0.66	Remote Similarity	NPD2843	Phase 2
0.6599	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7019	Approved
0.6593	Remote Similarity	NPD8016	Phase 3
0.6593	Remote Similarity	NPD4584	Approved
0.6593	Remote Similarity	NPD7020	Approved
0.6593	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8149	Discontinued
0.6587	Remote Similarity	NPD4040	Phase 1
0.6576	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3141	Discontinued
0.6575	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7752	Approved
0.6573	Remote Similarity	NPD7753	Approved
0.6571	Remote Similarity	NPD2916	Discontinued
0.6567	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4424	Discontinued
0.6559	Remote Similarity	NPD2672	Discontinued
0.6559	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6677	Suspended
0.6556	Remote Similarity	NPD5754	Discontinued
0.6555	Remote Similarity	NPD6905	Phase 2
0.6554	Remote Similarity	NPD822	Approved
0.6553	Remote Similarity	NPD5457	Discontinued
0.6552	Remote Similarity	NPD2245	Discovery
0.6552	Remote Similarity	NPD7256	Discontinued

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