NPASS Compound

Structure

NPC207971 OpenBabel07101718322D 26 29 0 0 0 0 0 0 0 0999 V2000 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 16 2 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.22
Volume:	525.066
LogP:	0.892
LogD:	0.73
LogS:	-3.368
# Rotatable Bonds:	7
TPSA:	182.19
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	5.231
Fsp3:	0.741
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.753
MDCK Permeability:	0.00010243029828416184
Pgp-inhibitor:	0.091
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.796
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	64.53609466552734%
Volume Distribution (VD):	0.717
Pgp-substrate:	25.568899154663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	2.742
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.258
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.062
Carcinogencity:	0.86
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC207971

Natural Product ID:	NPC207971
*Common Name:**	N-Ethoxycarbonylpropylcrinasiadine
IUPAC Name:	ethyl 4-(6-oxo-[1,3]dioxolo[4,5-j]phenanthridin-5-yl)butanoate
Synonyms:	N-Ethoxycarbonylpropylcrinasiadine
Standard InCHIKey:	BUFRNEZYXLPJJR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO5/c1-2-24-19(22)8-5-9-21-16-7-4-3-6-13(16)14-10-17-18(26-12-25-17)11-15(14)20(21)23/h3-4,6-7,10-11H,2,5,8-9,12H2,1H3
SMILES:	CCOC(=O)CCCn1c2ccccc2c2cc3c(cc2c1=O)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208198
PubChem CID:	71454342
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae 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
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	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	6

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[547811]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[547811]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[547811]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[547811]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[547811]
NPT27	Others	Unspecified		IC50	=	36000.0	nM	PMID[547811]

☑ 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 NPC207971 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	459
0.1-0.2	2419
0.2-0.3	10230
0.3-0.4	7043
0.4-0.5	11085
0.5-0.6	8889
0.6-0.7	2107
0.7-0.8	413
0.8-0.85	35
0.85-0.9	9
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC268077
0.9613	High Similarity	NPC71124
0.95	High Similarity	NPC254957
0.9454	High Similarity	NPC5374
0.8878	High Similarity	NPC55470
0.852	High Similarity	NPC308943
0.8333	Intermediate Similarity	NPC24954
0.829	Intermediate Similarity	NPC477258
0.828	Intermediate Similarity	NPC5167
0.828	Intermediate Similarity	NPC85613
0.8263	Intermediate Similarity	NPC169387
0.8263	Intermediate Similarity	NPC477259
0.8254	Intermediate Similarity	NPC116007
0.8205	Intermediate Similarity	NPC23080
0.8205	Intermediate Similarity	NPC193906
0.82	Intermediate Similarity	NPC207873
0.82	Intermediate Similarity	NPC100573
0.8191	Intermediate Similarity	NPC27887
0.815	Intermediate Similarity	NPC222561
0.8063	Intermediate Similarity	NPC83511
0.8021	Intermediate Similarity	NPC303581
0.8021	Intermediate Similarity	NPC67978
0.8011	Intermediate Similarity	NPC86469
0.8	Intermediate Similarity	NPC253675
0.7989	Intermediate Similarity	NPC287588
0.797	Intermediate Similarity	NPC24228
0.7952	Intermediate Similarity	NPC148124
0.7951	Intermediate Similarity	NPC10732
0.7949	Intermediate Similarity	NPC226708
0.7937	Intermediate Similarity	NPC308267
0.7931	Intermediate Similarity	NPC90185
0.7929	Intermediate Similarity	NPC14622
0.7929	Intermediate Similarity	NPC70290
0.7929	Intermediate Similarity	NPC46744
0.7929	Intermediate Similarity	NPC73020
0.7929	Intermediate Similarity	NPC124302
0.7929	Intermediate Similarity	NPC215098
0.7925	Intermediate Similarity	NPC476436
0.7905	Intermediate Similarity	NPC99724
0.7895	Intermediate Similarity	NPC283810
0.7895	Intermediate Similarity	NPC222524
0.7889	Intermediate Similarity	NPC119669
0.7874	Intermediate Similarity	NPC298449
0.7865	Intermediate Similarity	NPC179704
0.785	Intermediate Similarity	NPC120671
0.785	Intermediate Similarity	NPC226652
0.785	Intermediate Similarity	NPC314100
0.785	Intermediate Similarity	NPC72788
0.7834	Intermediate Similarity	NPC476220
0.7834	Intermediate Similarity	NPC160113
0.7824	Intermediate Similarity	NPC249405
0.7822	Intermediate Similarity	NPC41216
0.7804	Intermediate Similarity	NPC248903
0.7801	Intermediate Similarity	NPC35680
0.7798	Intermediate Similarity	NPC154922
0.7778	Intermediate Similarity	NPC469816
0.7778	Intermediate Similarity	NPC469815
0.7772	Intermediate Similarity	NPC202771
0.7772	Intermediate Similarity	NPC2173
0.7772	Intermediate Similarity	NPC328700
0.7772	Intermediate Similarity	NPC119818
0.7762	Intermediate Similarity	NPC195120
0.7762	Intermediate Similarity	NPC87560
0.776	Intermediate Similarity	NPC121400
0.7757	Intermediate Similarity	NPC26928
0.7755	Intermediate Similarity	NPC312531
0.7755	Intermediate Similarity	NPC141440
0.7754	Intermediate Similarity	NPC231198
0.7742	Intermediate Similarity	NPC476429
0.7739	Intermediate Similarity	NPC33256
0.7729	Intermediate Similarity	NPC186569
0.7729	Intermediate Similarity	NPC61731
0.7727	Intermediate Similarity	NPC302001
0.7711	Intermediate Similarity	NPC207239
0.7705	Intermediate Similarity	NPC470708
0.7696	Intermediate Similarity	NPC38961
0.7692	Intermediate Similarity	NPC304837
0.7692	Intermediate Similarity	NPC476258
0.7656	Intermediate Similarity	NPC227361
0.7656	Intermediate Similarity	NPC124658
0.765	Intermediate Similarity	NPC125924
0.7647	Intermediate Similarity	NPC153631
0.7644	Intermediate Similarity	NPC82541
0.7641	Intermediate Similarity	NPC102760
0.7632	Intermediate Similarity	NPC241055
0.763	Intermediate Similarity	NPC313327
0.7624	Intermediate Similarity	NPC475959
0.7623	Intermediate Similarity	NPC113455
0.7608	Intermediate Similarity	NPC159815
0.7606	Intermediate Similarity	NPC157983
0.7606	Intermediate Similarity	NPC118154
0.7594	Intermediate Similarity	NPC135006
0.7576	Intermediate Similarity	NPC237579
0.7576	Intermediate Similarity	NPC208890
0.7576	Intermediate Similarity	NPC474904
0.7576	Intermediate Similarity	NPC166979
0.7576	Intermediate Similarity	NPC45389
0.7574	Intermediate Similarity	NPC17677
0.7574	Intermediate Similarity	NPC100863
0.7563	Intermediate Similarity	NPC21425
0.7548	Intermediate Similarity	NPC85661
0.7525	Intermediate Similarity	NPC162694
0.7524	Intermediate Similarity	NPC475147
0.7524	Intermediate Similarity	NPC470481
0.7524	Intermediate Similarity	NPC470482
0.7522	Intermediate Similarity	NPC120239
0.7513	Intermediate Similarity	NPC285941
0.75	Intermediate Similarity	NPC473004
0.75	Intermediate Similarity	NPC46679
0.75	Intermediate Similarity	NPC474708
0.7487	Intermediate Similarity	NPC471604
0.7486	Intermediate Similarity	NPC470088
0.7477	Intermediate Similarity	NPC256422
0.7475	Intermediate Similarity	NPC162653
0.7475	Intermediate Similarity	NPC470646
0.7474	Intermediate Similarity	NPC306669
0.7473	Intermediate Similarity	NPC93593
0.7466	Intermediate Similarity	NPC22481
0.7465	Intermediate Similarity	NPC126556
0.7465	Intermediate Similarity	NPC195636
0.7464	Intermediate Similarity	NPC171882
0.7464	Intermediate Similarity	NPC475133
0.7464	Intermediate Similarity	NPC121510
0.7461	Intermediate Similarity	NPC227683
0.7453	Intermediate Similarity	NPC146976
0.7451	Intermediate Similarity	NPC267414
0.7448	Intermediate Similarity	NPC475845
0.7447	Intermediate Similarity	NPC106786
0.7421	Intermediate Similarity	NPC59567
0.7421	Intermediate Similarity	NPC476569
0.7413	Intermediate Similarity	NPC63152
0.7407	Intermediate Similarity	NPC46259
0.7406	Intermediate Similarity	NPC236668
0.7402	Intermediate Similarity	NPC112937
0.7398	Intermediate Similarity	NPC190461
0.7396	Intermediate Similarity	NPC57812
0.7396	Intermediate Similarity	NPC474324
0.7394	Intermediate Similarity	NPC93653
0.7393	Intermediate Similarity	NPC295479
0.7393	Intermediate Similarity	NPC220241
0.7385	Intermediate Similarity	NPC231924
0.7382	Intermediate Similarity	NPC168409
0.7381	Intermediate Similarity	NPC46990
0.738	Intermediate Similarity	NPC138487
0.738	Intermediate Similarity	NPC41178
0.738	Intermediate Similarity	NPC216459
0.7379	Intermediate Similarity	NPC471489
0.7368	Intermediate Similarity	NPC299582
0.7366	Intermediate Similarity	NPC233029
0.7366	Intermediate Similarity	NPC210148
0.7366	Intermediate Similarity	NPC189903
0.7366	Intermediate Similarity	NPC182907
0.7363	Intermediate Similarity	NPC469978
0.7361	Intermediate Similarity	NPC318525
0.7361	Intermediate Similarity	NPC476069
0.7361	Intermediate Similarity	NPC10653
0.7358	Intermediate Similarity	NPC91234
0.7351	Intermediate Similarity	NPC223125
0.735	Intermediate Similarity	NPC230098
0.735	Intermediate Similarity	NPC471650
0.7346	Intermediate Similarity	NPC269449
0.734	Intermediate Similarity	NPC146288
0.7333	Intermediate Similarity	NPC4669
0.733	Intermediate Similarity	NPC127178
0.733	Intermediate Similarity	NPC278525
0.733	Intermediate Similarity	NPC138830
0.7327	Intermediate Similarity	NPC128476
0.7324	Intermediate Similarity	NPC268223
0.7321	Intermediate Similarity	NPC477161
0.7321	Intermediate Similarity	NPC108342
0.7321	Intermediate Similarity	NPC80472
0.7316	Intermediate Similarity	NPC232924
0.7316	Intermediate Similarity	NPC477559
0.7316	Intermediate Similarity	NPC266753
0.7316	Intermediate Similarity	NPC306902
0.7316	Intermediate Similarity	NPC160298
0.7296	Intermediate Similarity	NPC287152
0.7291	Intermediate Similarity	NPC94499
0.729	Intermediate Similarity	NPC290227
0.7286	Intermediate Similarity	NPC473007
0.7282	Intermediate Similarity	NPC212163
0.7277	Intermediate Similarity	NPC119722
0.7273	Intermediate Similarity	NPC148898
0.7273	Intermediate Similarity	NPC474745
0.7273	Intermediate Similarity	NPC223124
0.7273	Intermediate Similarity	NPC220961
0.7269	Intermediate Similarity	NPC77777
0.7264	Intermediate Similarity	NPC477186
0.7263	Intermediate Similarity	NPC477080
0.7256	Intermediate Similarity	NPC240684
0.7255	Intermediate Similarity	NPC230313
0.7254	Intermediate Similarity	NPC24264
0.7254	Intermediate Similarity	NPC476432
0.725	Intermediate Similarity	NPC33902
0.725	Intermediate Similarity	NPC276674
0.7249	Intermediate Similarity	NPC31311
0.7249	Intermediate Similarity	NPC234392
0.7246	Intermediate Similarity	NPC67904
0.7244	Intermediate Similarity	NPC291173
0.7238	Intermediate Similarity	NPC328750

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 NPC207971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	665
0.2-0.3	902
0.3-0.4	1417
0.4-0.5	2603
0.5-0.6	2305
0.6-0.7	835
0.7-0.8	141
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8299	Intermediate Similarity	NPD5071	Phase 2
0.795	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4859	Phase 1
0.7929	Intermediate Similarity	NPD4420	Approved
0.7903	Intermediate Similarity	NPD5183	Approved
0.7903	Intermediate Similarity	NPD5186	Approved
0.7795	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD5005	Approved
0.7772	Intermediate Similarity	NPD5006	Approved
0.7767	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4846	Phase 2
0.7676	Intermediate Similarity	NPD5978	Approved
0.7676	Intermediate Similarity	NPD5977	Approved
0.767	Intermediate Similarity	NPD5950	Discontinued
0.765	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6625	Approved
0.7608	Intermediate Similarity	NPD7225	Discontinued
0.7606	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5313	Approved
0.7604	Intermediate Similarity	NPD5312	Approved
0.7583	Intermediate Similarity	NPD5025	Approved
0.7566	Intermediate Similarity	NPD6457	Approved
0.7563	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD683	Approved
0.7555	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7281	Phase 3
0.75	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD8149	Discontinued
0.7488	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5582	Discontinued
0.7462	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5564	Approved
0.7437	Intermediate Similarity	NPD7291	Discontinued
0.7421	Intermediate Similarity	NPD4885	Approved
0.7419	Intermediate Similarity	NPD7279	Phase 2
0.7419	Intermediate Similarity	NPD6385	Approved
0.7419	Intermediate Similarity	NPD7278	Phase 2
0.7419	Intermediate Similarity	NPD6386	Approved
0.7406	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6321	Discontinued
0.7374	Intermediate Similarity	NPD6853	Approved
0.7374	Intermediate Similarity	NPD6618	Phase 2
0.7374	Intermediate Similarity	NPD6851	Approved
0.7366	Intermediate Similarity	NPD1880	Phase 3
0.7347	Intermediate Similarity	NPD6297	Approved
0.7333	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4107	Approved
0.7326	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7110	Phase 1
0.7316	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6716	Phase 1
0.7308	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5242	Approved
0.7295	Intermediate Similarity	NPD6238	Discontinued
0.729	Intermediate Similarity	NPD7559	Phase 2
0.7281	Intermediate Similarity	NPD3437	Discontinued
0.7273	Intermediate Similarity	NPD7223	Discontinued
0.7273	Intermediate Similarity	NPD7224	Discontinued
0.7264	Intermediate Similarity	NPD3349	Phase 2
0.7246	Intermediate Similarity	NPD5457	Discontinued
0.7245	Intermediate Similarity	NPD5600	Discontinued
0.7238	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD824	Approved
0.7212	Intermediate Similarity	NPD4482	Phase 3
0.7204	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3641	Approved
0.7204	Intermediate Similarity	NPD3639	Approved
0.7204	Intermediate Similarity	NPD1670	Discontinued
0.7204	Intermediate Similarity	NPD3640	Phase 3
0.7202	Intermediate Similarity	NPD2821	Approved
0.7182	Intermediate Similarity	NPD3912	Discontinued
0.7173	Intermediate Similarity	NPD7708	Approved
0.7172	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6723	Discontinued
0.7143	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3964	Approved
0.7115	Intermediate Similarity	NPD6874	Approved
0.7112	Intermediate Similarity	NPD6031	Approved
0.7112	Intermediate Similarity	NPD6030	Approved
0.7098	Intermediate Similarity	NPD4952	Phase 3
0.7095	Intermediate Similarity	NPD7627	Approved
0.7095	Intermediate Similarity	NPD7626	Approved
0.709	Intermediate Similarity	NPD6876	Approved
0.709	Intermediate Similarity	NPD6875	Approved
0.7087	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6493	Phase 3
0.7085	Intermediate Similarity	NPD4328	Approved
0.7077	Intermediate Similarity	NPD4166	Phase 2
0.7065	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2492	Phase 1
0.7054	Intermediate Similarity	NPD7803	Approved
0.7051	Intermediate Similarity	NPD3257	Approved
0.7047	Intermediate Similarity	NPD1307	Phase 2
0.7047	Intermediate Similarity	NPD1309	Phase 2
0.7035	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD2681	Approved
0.7026	Intermediate Similarity	NPD6107	Approved
0.7026	Intermediate Similarity	NPD2680	Approved
0.7023	Intermediate Similarity	NPD5860	Discontinued
0.7014	Intermediate Similarity	NPD7805	Phase 3
0.701	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8027	Approved
0.7005	Intermediate Similarity	NPD4584	Approved
0.7004	Intermediate Similarity	NPD4373	Phase 2
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3258	Approved
0.7	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2899	Discontinued
0.7	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3965	Phase 1
0.6985	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2968	Approved
0.698	Remote Similarity	NPD2971	Approved
0.6976	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7186	Phase 3
0.6963	Remote Similarity	NPD6873	Phase 2
0.6959	Remote Similarity	NPD3816	Phase 1
0.6959	Remote Similarity	NPD3815	Phase 1
0.6957	Remote Similarity	NPD6181	Discontinued
0.6951	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5914	Approved
0.6942	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5515	Phase 2
0.6938	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3057	Approved
0.6926	Remote Similarity	NPD7885	Phase 2
0.6926	Remote Similarity	NPD7886	Phase 2
0.6923	Remote Similarity	NPD743	Approved
0.6919	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3290	Approved
0.6919	Remote Similarity	NPD5997	Discontinued
0.6919	Remote Similarity	NPD3289	Phase 3
0.6913	Remote Similarity	NPD5805	Approved
0.6898	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7546	Discontinued
0.6893	Remote Similarity	NPD5928	Phase 1
0.6892	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8463	Approved
0.6884	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8091	Phase 3
0.6872	Remote Similarity	NPD4981	Phase 2
0.6872	Remote Similarity	NPD3297	Approved
0.6866	Remote Similarity	NPD3920	Phase 2
0.6864	Remote Similarity	NPD8102	Discontinued
0.6854	Remote Similarity	NPD3533	Approved
0.6854	Remote Similarity	NPD3448	Approved
0.6854	Remote Similarity	NPD2972	Approved
0.6854	Remote Similarity	NPD2491	Approved
0.6853	Remote Similarity	NPD2249	Approved
0.6853	Remote Similarity	NPD2247	Approved
0.685	Remote Similarity	NPD7177	Discontinued
0.6849	Remote Similarity	NPD4356	Discontinued
0.6846	Remote Similarity	NPD7955	Approved
0.6846	Remote Similarity	NPD7956	Approved
0.6842	Remote Similarity	NPD3441	Approved
0.6842	Remote Similarity	NPD3442	Approved
0.6834	Remote Similarity	NPD4481	Phase 3
0.6833	Remote Similarity	NPD5980	Discovery
0.6831	Remote Similarity	NPD2670	Approved
0.683	Remote Similarity	NPD6997	Phase 2
0.683	Remote Similarity	NPD8311	Discontinued
0.6827	Remote Similarity	NPD3923	Approved
0.6827	Remote Similarity	NPD3922	Approved
0.6827	Remote Similarity	NPD3924	Approved
0.6827	Remote Similarity	NPD3921	Approved
0.6825	Remote Similarity	NPD7528	Approved
0.6818	Remote Similarity	NPD6228	Discontinued
0.6816	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7395	Discontinued
0.68	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3752	Phase 2
0.6796	Remote Similarity	NPD4515	Suspended
0.6795	Remote Similarity	NPD6517	Phase 3
0.6791	Remote Similarity	NPD3298	Approved
0.679	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3885	Approved
0.6781	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7668	Phase 2
0.6779	Remote Similarity	NPD2488	Approved
0.6779	Remote Similarity	NPD2490	Approved
0.6777	Remote Similarity	NPD2975	Approved
0.6777	Remote Similarity	NPD2974	Approved
0.6777	Remote Similarity	NPD2973	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