NPASS Compound

Structure

NPC473004 OpenBabel07101718332D 29 33 0 0 1 0 0 0 0 0999 V2000 6.1328 -0.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6391 -0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6106 0.6332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2524 2.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6210 2.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0959 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0125 0.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6115 1.8048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4610 0.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4135 1.8048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6316 0.6109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6109 0.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1109 2.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6360 0.8299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4135 1.8048 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6359 1.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2225 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5125 2.2387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0125 0.0481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9960 -0.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 0.8299 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5271 1.0559 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 1.5692 -0.3872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5089 -0.9481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9843 2.9488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6579 -0.7531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7900 1.0230 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 14 1 0 0 0 0 6 17 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 29 1 0 0 0 0 12 23 1 0 0 0 0 12 25 2 0 0 0 0 13 15 1 0 0 0 0 14 27 1 0 0 0 0 15 8 1 6 0 0 0 15 16 1 0 0 0 0 16 11 1 1 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 9 1 1 0 0 0 19 23 1 0 0 0 0 20 22 1 6 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 9 1 6 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.18
Volume:	396.412
LogP:	2.64
LogD:	2.5
LogS:	-4.672
# Rotatable Bonds:	3
TPSA:	68.31
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	6.364
Fsp3:	0.545
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:	-4.906
MDCK Permeability:	1.0622145055094734e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.548
Human Intestinal Absorption (HIA):	0.52
20% Bioavailability (F20%):	0.114
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	56.795188903808594%
Volume Distribution (VD):	1.139
Pgp-substrate:	25.590356826782227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.902
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.757
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	8.207
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.381
Carcinogencity:	0.921
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.552

Download Data

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

Natural Product: NPC473004

Natural Product ID:	NPC473004
*Common Name:**	CVZRLVRONXDZMM-JNIIIHBOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CVZRLVRONXDZMM-JNIIIHBOSA-N
Standard InCHI:	InChI=1S/C22H26N2O5/c1-4-13-10-23(12-25)19-9-22(20-8-15(13)16(19)11-29-20)17-6-5-14(27-2)7-18(17)24(28-3)21(22)26/h4-7,12,15-16,19-20H,8-11H2,1-3H3/b13-4+/t15-,16-,19-,20+,22-/m0/s1
SMILES:	CC=C1CN(C2CC3(C4CC1C2CO4)C5=C(C=C(C=C5)OC)N(C3=O)OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597660
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003758] Gelsemium alkaloids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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[564721]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[564721]

☑ 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 NPC473004 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	374
0.1-0.2	1619
0.2-0.3	6613
0.3-0.4	11138
0.4-0.5	16083
0.5-0.6	5868
0.6-0.7	916
0.7-0.8	71
0.8-0.85	5
0.85-0.9	4
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC230313
0.9425	High Similarity	NPC473008
0.9195	High Similarity	NPC473007
0.9106	High Similarity	NPC243626
0.8895	High Similarity	NPC473006
0.8824	High Similarity	NPC477161
0.8783	High Similarity	NPC477160
0.8663	High Similarity	NPC473005
0.8656	High Similarity	NPC67904
0.8571	High Similarity	NPC14339
0.8449	Intermediate Similarity	NPC100863
0.837	Intermediate Similarity	NPC473569
0.8363	Intermediate Similarity	NPC29285
0.8359	Intermediate Similarity	NPC10732
0.8265	Intermediate Similarity	NPC159815
0.8263	Intermediate Similarity	NPC138830
0.8171	Intermediate Similarity	NPC176983
0.798	Intermediate Similarity	NPC318525
0.798	Intermediate Similarity	NPC10653
0.7895	Intermediate Similarity	NPC204970
0.7882	Intermediate Similarity	NPC77777
0.7857	Intermediate Similarity	NPC41216
0.7795	Intermediate Similarity	NPC127178
0.7778	Intermediate Similarity	NPC21425
0.7765	Intermediate Similarity	NPC286871
0.7696	Intermediate Similarity	NPC174629
0.7696	Intermediate Similarity	NPC474059
0.7673	Intermediate Similarity	NPC82541
0.7656	Intermediate Similarity	NPC22476
0.7611	Intermediate Similarity	NPC143457
0.7568	Intermediate Similarity	NPC96901
0.7566	Intermediate Similarity	NPC477159
0.7549	Intermediate Similarity	NPC127996
0.75	Intermediate Similarity	NPC207971
0.7473	Intermediate Similarity	NPC139085
0.7473	Intermediate Similarity	NPC214626
0.7473	Intermediate Similarity	NPC251212
0.7463	Intermediate Similarity	NPC87714
0.7463	Intermediate Similarity	NPC268077
0.7447	Intermediate Similarity	NPC260075
0.7433	Intermediate Similarity	NPC13367
0.7424	Intermediate Similarity	NPC71124
0.7423	Intermediate Similarity	NPC22689
0.7423	Intermediate Similarity	NPC45389
0.7423	Intermediate Similarity	NPC105055
0.7406	Intermediate Similarity	NPC122886
0.7403	Intermediate Similarity	NPC113946
0.7389	Intermediate Similarity	NPC478075
0.7379	Intermediate Similarity	NPC264176
0.7379	Intermediate Similarity	NPC470481
0.7379	Intermediate Similarity	NPC470482
0.7376	Intermediate Similarity	NPC475147
0.7346	Intermediate Similarity	NPC46259
0.7336	Intermediate Similarity	NPC470480
0.7333	Intermediate Similarity	NPC288110
0.7317	Intermediate Similarity	NPC475133
0.7308	Intermediate Similarity	NPC189661
0.7306	Intermediate Similarity	NPC102760
0.7304	Intermediate Similarity	NPC198160
0.7297	Intermediate Similarity	NPC299582
0.7297	Intermediate Similarity	NPC472106
0.7296	Intermediate Similarity	NPC28510
0.729	Intermediate Similarity	NPC476436
0.7286	Intermediate Similarity	NPC161804
0.7283	Intermediate Similarity	NPC472120
0.7283	Intermediate Similarity	NPC472101
0.7277	Intermediate Similarity	NPC39822
0.7273	Intermediate Similarity	NPC234772
0.7273	Intermediate Similarity	NPC470001
0.7273	Intermediate Similarity	NPC470002
0.7251	Intermediate Similarity	NPC37957
0.7238	Intermediate Similarity	NPC195636
0.7238	Intermediate Similarity	NPC305984
0.7238	Intermediate Similarity	NPC126556
0.7222	Intermediate Similarity	NPC470485
0.7222	Intermediate Similarity	NPC254957
0.7214	Intermediate Similarity	NPC5374
0.7212	Intermediate Similarity	NPC116178
0.7208	Intermediate Similarity	NPC203628
0.7208	Intermediate Similarity	NPC1820
0.7204	Intermediate Similarity	NPC473041
0.7198	Intermediate Similarity	NPC269449
0.7198	Intermediate Similarity	NPC476651
0.7194	Intermediate Similarity	NPC477186
0.7189	Intermediate Similarity	NPC472117
0.7182	Intermediate Similarity	NPC291173
0.7177	Intermediate Similarity	NPC321166
0.7177	Intermediate Similarity	NPC217903
0.717	Intermediate Similarity	NPC219397
0.7166	Intermediate Similarity	NPC279527
0.7166	Intermediate Similarity	NPC214960
0.7165	Intermediate Similarity	NPC245741
0.7163	Intermediate Similarity	NPC231924
0.7149	Intermediate Similarity	NPC184680
0.7143	Intermediate Similarity	NPC74216
0.7143	Intermediate Similarity	NPC471648
0.7143	Intermediate Similarity	NPC232600
0.7136	Intermediate Similarity	NPC476069
0.7136	Intermediate Similarity	NPC203972
0.713	Intermediate Similarity	NPC266994
0.7129	Intermediate Similarity	NPC119722
0.7123	Intermediate Similarity	NPC476429
0.7122	Intermediate Similarity	NPC470484
0.7121	Intermediate Similarity	NPC470483
0.7117	Intermediate Similarity	NPC470785
0.7117	Intermediate Similarity	NPC470784
0.7117	Intermediate Similarity	NPC474183
0.7112	Intermediate Similarity	NPC70172
0.7111	Intermediate Similarity	NPC242000
0.7107	Intermediate Similarity	NPC284706
0.7105	Intermediate Similarity	NPC476425
0.7103	Intermediate Similarity	NPC128476
0.7097	Intermediate Similarity	NPC473458
0.7092	Intermediate Similarity	NPC282092
0.7091	Intermediate Similarity	NPC473105
0.7089	Intermediate Similarity	NPC153923
0.7087	Intermediate Similarity	NPC195787
0.7087	Intermediate Similarity	NPC246140
0.7081	Intermediate Similarity	NPC301163
0.7079	Intermediate Similarity	NPC112937
0.7079	Intermediate Similarity	NPC234933
0.707	Intermediate Similarity	NPC250960
0.707	Intermediate Similarity	NPC71539
0.707	Intermediate Similarity	NPC148124
0.7065	Intermediate Similarity	NPC303214
0.7064	Intermediate Similarity	NPC311906
0.7048	Intermediate Similarity	NPC472098
0.7043	Intermediate Similarity	NPC309531
0.7043	Intermediate Similarity	NPC472102
0.7032	Intermediate Similarity	NPC470821
0.7031	Intermediate Similarity	NPC129624
0.703	Intermediate Similarity	NPC272706
0.7029	Intermediate Similarity	NPC106606
0.7028	Intermediate Similarity	NPC152768
0.7028	Intermediate Similarity	NPC148183
0.7024	Intermediate Similarity	NPC474077
0.7023	Intermediate Similarity	NPC99724
0.7022	Intermediate Similarity	NPC308197
0.7021	Intermediate Similarity	NPC24954
0.7019	Intermediate Similarity	NPC205926
0.7018	Intermediate Similarity	NPC248903
0.7011	Intermediate Similarity	NPC161827
0.701	Intermediate Similarity	NPC222524
0.7009	Intermediate Similarity	NPC222046
0.7005	Intermediate Similarity	NPC21638
0.7005	Intermediate Similarity	NPC262725
0.7005	Intermediate Similarity	NPC19175
0.7	Intermediate Similarity	NPC114039
0.7	Intermediate Similarity	NPC206109
0.7	Intermediate Similarity	NPC469915
0.6995	Remote Similarity	NPC193906
0.6995	Remote Similarity	NPC476326
0.6995	Remote Similarity	NPC313327
0.6995	Remote Similarity	NPC23080
0.6989	Remote Similarity	NPC133817
0.6989	Remote Similarity	NPC476443
0.6986	Remote Similarity	NPC471561
0.6972	Remote Similarity	NPC26928
0.6965	Remote Similarity	NPC471825
0.6946	Remote Similarity	NPC475559
0.6944	Remote Similarity	NPC329830
0.6941	Remote Similarity	NPC471513
0.6939	Remote Similarity	NPC98197
0.6935	Remote Similarity	NPC169387
0.6935	Remote Similarity	NPC477259
0.6931	Remote Similarity	NPC471124
0.6927	Remote Similarity	NPC115588
0.6927	Remote Similarity	NPC73280
0.6923	Remote Similarity	NPC166169
0.6923	Remote Similarity	NPC70092
0.6919	Remote Similarity	NPC116007
0.6908	Remote Similarity	NPC473460
0.6907	Remote Similarity	NPC127082
0.6906	Remote Similarity	NPC160113
0.6906	Remote Similarity	NPC476220
0.69	Remote Similarity	NPC283207
0.6898	Remote Similarity	NPC263709
0.6898	Remote Similarity	NPC310403
0.6898	Remote Similarity	NPC63210
0.6898	Remote Similarity	NPC97380
0.6898	Remote Similarity	NPC243673
0.6898	Remote Similarity	NPC148468
0.689	Remote Similarity	NPC308943
0.6884	Remote Similarity	NPC96321
0.6884	Remote Similarity	NPC303658
0.6878	Remote Similarity	NPC477397
0.6875	Remote Similarity	NPC154922
0.6872	Remote Similarity	NPC321211
0.6869	Remote Similarity	NPC322621
0.6863	Remote Similarity	NPC162440
0.6863	Remote Similarity	NPC472191
0.6862	Remote Similarity	NPC93653
0.686	Remote Similarity	NPC15987
0.686	Remote Similarity	NPC295898
0.686	Remote Similarity	NPC52801
0.6859	Remote Similarity	NPC33507
0.6858	Remote Similarity	NPC475816
0.6857	Remote Similarity	NPC317709
0.6857	Remote Similarity	NPC475910
0.6857	Remote Similarity	NPC100573

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 NPC473004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	641
0.2-0.3	810
0.3-0.4	1691
0.4-0.5	3057
0.5-0.6	2333
0.6-0.7	371
0.7-0.8	20
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
0.779	Intermediate Similarity	NPD6457	Approved
0.7722	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD5183	Approved
0.765	Intermediate Similarity	NPD5186	Approved
0.7576	Intermediate Similarity	NPD6238	Discontinued
0.7571	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3437	Discontinued
0.7441	Intermediate Similarity	NPD3912	Discontinued
0.7396	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5313	Approved
0.7354	Intermediate Similarity	NPD5312	Approved
0.735	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8027	Approved
0.7268	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5600	Discontinued
0.7238	Intermediate Similarity	NPD6357	Discontinued
0.7173	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6321	Discontinued
0.7135	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5071	Phase 2
0.7062	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6644	Discontinued
0.703	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7821	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4166	Phase 2
0.7	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3793	Phase 3
0.6959	Remote Similarity	NPD7820	Phase 3
0.6959	Remote Similarity	NPD7479	Phase 2
0.6957	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4981	Phase 2
0.6952	Remote Similarity	NPD5967	Approved
0.6947	Remote Similarity	NPD3511	Discontinued
0.6947	Remote Similarity	NPD7126	Discontinued
0.6943	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3639	Approved
0.694	Remote Similarity	NPD3640	Phase 3
0.694	Remote Similarity	NPD3641	Approved
0.6923	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6790	Phase 1
0.6901	Remote Similarity	NPD5293	Phase 2
0.6895	Remote Similarity	NPD5823	Approved
0.6882	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6874	Approved
0.6875	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5994	Discontinued
0.6866	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7805	Phase 3
0.6863	Remote Similarity	NPD5515	Phase 2
0.6859	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3983	Phase 3
0.6859	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8359	Phase 2
0.6856	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1670	Discontinued
0.6842	Remote Similarity	NPD4796	Discontinued
0.6839	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD19	Approved
0.6825	Remote Similarity	NPD1743	Approved
0.6825	Remote Similarity	NPD1742	Approved
0.6822	Remote Similarity	NPD7559	Phase 2
0.6818	Remote Similarity	NPD7280	Phase 3
0.6818	Remote Similarity	NPD7281	Phase 3
0.6816	Remote Similarity	NPD7752	Approved
0.6816	Remote Similarity	NPD5114	Approved
0.6816	Remote Similarity	NPD5113	Approved
0.6816	Remote Similarity	NPD5112	Approved
0.6816	Remote Similarity	NPD7753	Approved
0.6814	Remote Similarity	NPD5582	Discontinued
0.68	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5025	Approved
0.6782	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6107	Approved
0.6755	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1769	Discontinued
0.6751	Remote Similarity	NPD6879	Phase 2
0.6751	Remote Similarity	NPD6878	Phase 2
0.6746	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD3591	Approved
0.6745	Remote Similarity	NPD3592	Approved
0.6742	Remote Similarity	NPD7186	Phase 3
0.6742	Remote Similarity	NPD743	Approved
0.6742	Remote Similarity	NPD7426	Phase 1
0.6738	Remote Similarity	NPD5617	Suspended
0.6736	Remote Similarity	NPD5847	Phase 1
0.6721	Remote Similarity	NPD3141	Discontinued
0.6719	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1294	Discontinued
0.6714	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8016	Phase 3
0.6711	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1307	Phase 2
0.6702	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1309	Phase 2
0.6702	Remote Similarity	NPD7110	Phase 1
0.6699	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7627	Approved
0.6699	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7626	Approved
0.6698	Remote Similarity	NPD4154	Approved
0.6683	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5601	Phase 2
0.6667	Remote Similarity	NPD2246	Approved
0.6667	Remote Similarity	NPD5997	Discontinued
0.6667	Remote Similarity	NPD4885	Approved
0.6667	Remote Similarity	NPD2248	Approved
0.6651	Remote Similarity	NPD7225	Discontinued
0.6651	Remote Similarity	NPD3416	Discontinued
0.6649	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5562	Approved
0.6636	Remote Similarity	NPD5561	Approved
0.6636	Remote Similarity	NPD7556	Discontinued
0.6635	Remote Similarity	NPD1880	Phase 3
0.6635	Remote Similarity	NPD4465	Phase 2
0.6635	Remote Similarity	NPD4467	Phase 2
0.6634	Remote Similarity	NPD4515	Suspended
0.6634	Remote Similarity	NPD4539	Phase 1
0.6632	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD2904	Discontinued
0.6632	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.663	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4846	Phase 2
0.6621	Remote Similarity	NPD5496	Approved
0.6617	Remote Similarity	NPD6851	Approved
0.6617	Remote Similarity	NPD6853	Approved
0.6615	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD848	Approved
0.6609	Remote Similarity	NPD850	Approved
0.6609	Remote Similarity	NPD849	Approved
0.6604	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7291	Discontinued
0.6601	Remote Similarity	NPD8025	Phase 2
0.66	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3479	Discontinued
0.6585	Remote Similarity	NPD5937	Approved
0.6583	Remote Similarity	NPD6297	Approved
0.6579	Remote Similarity	NPD7248	Discontinued
0.6578	Remote Similarity	NPD4952	Phase 3
0.6577	Remote Similarity	NPD7279	Phase 2
0.6577	Remote Similarity	NPD7278	Phase 2
0.6574	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3964	Approved
0.657	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7877	Suspended
0.656	Remote Similarity	NPD8149	Discontinued
0.6559	Remote Similarity	NPD4584	Approved
0.6555	Remote Similarity	NPD3297	Approved
0.6548	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5658	Approved
0.654	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6551	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4773	Phase 2
0.6526	Remote Similarity	NPD4772	Phase 2
0.6522	Remote Similarity	NPD4418	Discontinued
0.652	Remote Similarity	NPD3398	Discontinued
0.6517	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6716	Phase 1
0.6508	Remote Similarity	NPD4120	Approved
0.6508	Remote Similarity	NPD4121	Phase 3
0.6508	Remote Similarity	NPD5811	Approved
0.6507	Remote Similarity	NPD4668	Phase 2
0.6505	Remote Similarity	NPD5587	Approved
0.6505	Remote Similarity	NPD3124	Discontinued
0.6502	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7956	Approved
0.65	Remote Similarity	NPD7955	Approved
0.6497	Remote Similarity	NPD5858	Discontinued
0.6494	Remote Similarity	NPD7560	Approved
0.6491	Remote Similarity	NPD4373	Phase 2
0.6491	Remote Similarity	NPD6723	Discontinued
0.649	Remote Similarity	NPD5512	Phase 3
0.649	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2971	Approved
0.6485	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2968	Approved
0.6479	Remote Similarity	NPD3298	Approved
0.6476	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7811	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