NPASS Compound

Structure

NPC177261 OpenBabel07101718302D 22 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -0.5181 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 -2.3523 -1.3271 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 -2.5334 0.3955 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 -1.3578 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 1.8090 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 -1.5388 0.5000 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 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 -0.9511 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 2.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 1 0 0 0 15 19 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 9 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.08
Volume:	287.078
LogP:	3.179
LogD:	2.697
LogS:	-5.444
# Rotatable Bonds:	0
TPSA:	58.64
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	3.997
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	5.760711428592913e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.214

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	61.91771697998047%
Volume Distribution (VD):	0.865
Pgp-substrate:	38.81859588623047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.692
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.53
CYP3A4-inhibitor:	0.612
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	2.496
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.339
Carcinogencity:	0.851
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.468

Download Data

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

Natural Product: NPC177261

Natural Product ID:	NPC177261
*Common Name:**	Phaitanthrin D
IUPAC Name:	n.a.
Synonyms:	Phaitanthrin D
Standard InCHIKey:	YVTWVVANWZQLQY-WMLDXEAASA-N
Standard InCHI:	InChI=1S/C17H12N2O3/c20-15-10-5-1-3-7-12(10)18-17-9-22-16(21)14(17)11-6-2-4-8-13(11)19(15)17/h1-8,14,18H,9H2/t14-,17+/m0/s1
SMILES:	O=C1OC[C@@]23[C@H]1c1ccccc1N3C(=O)c1c(N2)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509375
PubChem CID:	44561298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO4147	Phaius mishmensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18507473]
NPO4147	Phaius mishmensis	Species	Orchidaceae	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	3

Activity Type	# Activity
Cell Line	3

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[470310]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[470310]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[470310]

☑ 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 NPC177261 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	293
0.1-0.2	1944
0.2-0.3	8825
0.3-0.4	17715
0.4-0.5	10170
0.5-0.6	3167
0.6-0.7	535
0.7-0.8	47
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7874	Intermediate Similarity	NPC470548
0.7714	Intermediate Similarity	NPC285622
0.7656	Intermediate Similarity	NPC285192
0.7614	Intermediate Similarity	NPC471197
0.7576	Intermediate Similarity	NPC471198
0.7542	Intermediate Similarity	NPC475094
0.75	Intermediate Similarity	NPC472118
0.7486	Intermediate Similarity	NPC214960
0.7486	Intermediate Similarity	NPC279527
0.7486	Intermediate Similarity	NPC182131
0.7458	Intermediate Similarity	NPC355
0.7446	Intermediate Similarity	NPC473815
0.7391	Intermediate Similarity	NPC473615
0.7351	Intermediate Similarity	NPC229484
0.7337	Intermediate Similarity	NPC259626
0.7333	Intermediate Similarity	NPC243850
0.7316	Intermediate Similarity	NPC472541
0.7316	Intermediate Similarity	NPC472542
0.7314	Intermediate Similarity	NPC176983
0.7314	Intermediate Similarity	NPC286871
0.7312	Intermediate Similarity	NPC292675
0.7299	Intermediate Similarity	NPC193410
0.7283	Intermediate Similarity	NPC2933
0.7273	Intermediate Similarity	NPC473298
0.7264	Intermediate Similarity	NPC244425
0.7264	Intermediate Similarity	NPC15384
0.7263	Intermediate Similarity	NPC472540
0.7263	Intermediate Similarity	NPC472539
0.7263	Intermediate Similarity	NPC470787
0.7258	Intermediate Similarity	NPC14994
0.7257	Intermediate Similarity	NPC248117
0.7257	Intermediate Similarity	NPC309531
0.7257	Intermediate Similarity	NPC472102
0.7243	Intermediate Similarity	NPC322621
0.7241	Intermediate Similarity	NPC113946
0.7241	Intermediate Similarity	NPC61013
0.7234	Intermediate Similarity	NPC25401
0.7228	Intermediate Similarity	NPC256288
0.7228	Intermediate Similarity	NPC159963
0.7216	Intermediate Similarity	NPC282339
0.7216	Intermediate Similarity	NPC99632
0.7193	Intermediate Similarity	NPC473329
0.7188	Intermediate Similarity	NPC209389
0.7184	Intermediate Similarity	NPC29285
0.7166	Intermediate Similarity	NPC181928
0.7157	Intermediate Similarity	NPC472538
0.7151	Intermediate Similarity	NPC223595
0.7151	Intermediate Similarity	NPC224970
0.7151	Intermediate Similarity	NPC167724
0.7107	Intermediate Similarity	NPC225400
0.7102	Intermediate Similarity	NPC36495
0.7071	Intermediate Similarity	NPC471155
0.7071	Intermediate Similarity	NPC470786
0.7065	Intermediate Similarity	NPC475761
0.7065	Intermediate Similarity	NPC321211
0.7062	Intermediate Similarity	NPC106118
0.7062	Intermediate Similarity	NPC225319
0.7059	Intermediate Similarity	NPC248601
0.7049	Intermediate Similarity	NPC264482
0.7049	Intermediate Similarity	NPC203202
0.7045	Intermediate Similarity	NPC123241
0.7043	Intermediate Similarity	NPC477159
0.7039	Intermediate Similarity	NPC472106
0.7035	Intermediate Similarity	NPC270241
0.7035	Intermediate Similarity	NPC237649
0.7035	Intermediate Similarity	NPC300596
0.7027	Intermediate Similarity	NPC475685
0.7025	Intermediate Similarity	NPC268534
0.7022	Intermediate Similarity	NPC472101
0.7022	Intermediate Similarity	NPC293458
0.7022	Intermediate Similarity	NPC472120
0.7011	Intermediate Similarity	NPC474081
0.7011	Intermediate Similarity	NPC117032
0.7006	Intermediate Similarity	NPC471122
0.6995	Remote Similarity	NPC475594
0.6981	Remote Similarity	NPC254698
0.6973	Remote Similarity	NPC6974
0.6973	Remote Similarity	NPC99043
0.6973	Remote Similarity	NPC218594
0.6971	Remote Similarity	NPC295021
0.6957	Remote Similarity	NPC475607
0.6944	Remote Similarity	NPC471124
0.6943	Remote Similarity	NPC34717
0.6928	Remote Similarity	NPC173295
0.6927	Remote Similarity	NPC472117
0.6919	Remote Similarity	NPC186669
0.6902	Remote Similarity	NPC13367
0.6889	Remote Similarity	NPC113056
0.6889	Remote Similarity	NPC138293
0.6886	Remote Similarity	NPC471123
0.6882	Remote Similarity	NPC474041
0.6872	Remote Similarity	NPC90967
0.6872	Remote Similarity	NPC471199
0.6872	Remote Similarity	NPC201424
0.6834	Remote Similarity	NPC295548
0.6834	Remote Similarity	NPC477179
0.6824	Remote Similarity	NPC43477
0.6816	Remote Similarity	NPC478075
0.6811	Remote Similarity	NPC469726
0.6811	Remote Similarity	NPC329338
0.6805	Remote Similarity	NPC469560
0.68	Remote Similarity	NPC254850
0.68	Remote Similarity	NPC477178
0.68	Remote Similarity	NPC477181
0.68	Remote Similarity	NPC477180
0.6789	Remote Similarity	NPC49184
0.6784	Remote Similarity	NPC471436
0.6782	Remote Similarity	NPC471950
0.6782	Remote Similarity	NPC471945
0.678	Remote Similarity	NPC478076
0.6778	Remote Similarity	NPC143457
0.6778	Remote Similarity	NPC68650
0.6778	Remote Similarity	NPC474058
0.6766	Remote Similarity	NPC470490
0.6766	Remote Similarity	NPC277350
0.6766	Remote Similarity	NPC477174
0.6766	Remote Similarity	NPC477173
0.6766	Remote Similarity	NPC253476
0.6765	Remote Similarity	NPC242933
0.6765	Remote Similarity	NPC207554
0.676	Remote Similarity	NPC222029
0.6757	Remote Similarity	NPC476425
0.6751	Remote Similarity	NPC100863
0.6749	Remote Similarity	NPC471951
0.6749	Remote Similarity	NPC471946
0.6742	Remote Similarity	NPC161827
0.674	Remote Similarity	NPC85651
0.6737	Remote Similarity	NPC471742
0.6737	Remote Similarity	NPC97584
0.6733	Remote Similarity	NPC470488
0.6725	Remote Similarity	NPC471164
0.6722	Remote Similarity	NPC276085
0.6721	Remote Similarity	NPC472114
0.6721	Remote Similarity	NPC472115
0.6716	Remote Similarity	NPC475359
0.6716	Remote Similarity	NPC191817
0.6703	Remote Similarity	NPC189116
0.6702	Remote Similarity	NPC52262
0.67	Remote Similarity	NPC475259
0.67	Remote Similarity	NPC470491
0.6685	Remote Similarity	NPC315368
0.6684	Remote Similarity	NPC470317
0.6684	Remote Similarity	NPC284706
0.6683	Remote Similarity	NPC214428
0.6667	Remote Similarity	NPC214626
0.6667	Remote Similarity	NPC316104
0.6667	Remote Similarity	NPC139085
0.6667	Remote Similarity	NPC251212
0.6667	Remote Similarity	NPC66936
0.6667	Remote Similarity	NPC141612
0.6667	Remote Similarity	NPC153694
0.6667	Remote Similarity	NPC17273
0.6667	Remote Similarity	NPC135601
0.6667	Remote Similarity	NPC211525
0.6667	Remote Similarity	NPC162417
0.6648	Remote Similarity	NPC472121
0.663	Remote Similarity	NPC310403
0.663	Remote Similarity	NPC63210
0.663	Remote Similarity	NPC243673
0.663	Remote Similarity	NPC263709
0.663	Remote Similarity	NPC97380
0.663	Remote Similarity	NPC148468
0.6627	Remote Similarity	NPC194562
0.6626	Remote Similarity	NPC226794
0.6612	Remote Similarity	NPC313757
0.6608	Remote Similarity	NPC319645
0.66	Remote Similarity	NPC475489
0.6596	Remote Similarity	NPC129624
0.6596	Remote Similarity	NPC476441
0.6584	Remote Similarity	NPC179605
0.6584	Remote Similarity	NPC279385
0.658	Remote Similarity	NPC282092
0.6578	Remote Similarity	NPC96901
0.6576	Remote Similarity	NPC470069
0.6576	Remote Similarity	NPC52059
0.6573	Remote Similarity	NPC243756
0.6571	Remote Similarity	NPC77777
0.657	Remote Similarity	NPC315051
0.657	Remote Similarity	NPC130251
0.6566	Remote Similarity	NPC122235
0.6566	Remote Similarity	NPC472116
0.6564	Remote Similarity	NPC473569
0.6564	Remote Similarity	NPC329858
0.6564	Remote Similarity	NPC45389
0.6562	Remote Similarity	NPC472119
0.6552	Remote Similarity	NPC268077
0.655	Remote Similarity	NPC122553
0.6543	Remote Similarity	NPC257490
0.6543	Remote Similarity	NPC103292
0.6535	Remote Similarity	NPC162730
0.6534	Remote Similarity	NPC264589
0.6529	Remote Similarity	NPC300299
0.6528	Remote Similarity	NPC307396
0.6524	Remote Similarity	NPC192533
0.6519	Remote Similarity	NPC63370
0.6519	Remote Similarity	NPC36836
0.6517	Remote Similarity	NPC318086
0.6514	Remote Similarity	NPC136002
0.6512	Remote Similarity	NPC83214
0.6508	Remote Similarity	NPC471743

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 NPC177261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	557
0.2-0.3	839
0.3-0.4	1500
0.4-0.5	3705
0.5-0.6	2102
0.6-0.7	252
0.7-0.8	10
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
0.7294	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1626	Approved
0.7186	Intermediate Similarity	NPD2365	Approved
0.7143	Intermediate Similarity	NPD2820	Phase 3
0.7143	Intermediate Similarity	NPD5042	Phase 1
0.7127	Intermediate Similarity	NPD7854	Phase 2
0.7073	Intermediate Similarity	NPD5185	Approved
0.7073	Intermediate Similarity	NPD5184	Approved
0.7073	Intermediate Similarity	NPD5182	Approved
0.7041	Intermediate Similarity	NPD1625	Approved
0.7035	Intermediate Similarity	NPD4888	Discontinued
0.7024	Intermediate Similarity	NPD3625	Discontinued
0.7011	Intermediate Similarity	NPD3248	Phase 1
0.6977	Remote Similarity	NPD1802	Approved
0.6977	Remote Similarity	NPD1801	Approved
0.6944	Remote Similarity	NPD5430	Discontinued
0.691	Remote Similarity	NPD33	Approved
0.691	Remote Similarity	NPD4393	Approved
0.6909	Remote Similarity	NPD1527	Phase 2
0.6893	Remote Similarity	NPD2836	Approved
0.6889	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1189	Approved
0.6839	Remote Similarity	NPD5942	Approved
0.6839	Remote Similarity	NPD5941	Approved
0.6834	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5993	Phase 1
0.6796	Remote Similarity	NPD3790	Phase 2
0.678	Remote Similarity	NPD2790	Discontinued
0.6778	Remote Similarity	NPD4311	Approved
0.6743	Remote Similarity	NPD4161	Discontinued
0.6739	Remote Similarity	NPD5183	Approved
0.6739	Remote Similarity	NPD5186	Approved
0.6727	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5918	Discontinued
0.6704	Remote Similarity	NPD7105	Phase 1
0.6703	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1574	Approved
0.6685	Remote Similarity	NPD5086	Approved
0.6667	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5856	Discontinued
0.6649	Remote Similarity	NPD3792	Approved
0.6647	Remote Similarity	NPD6342	Discontinued
0.6647	Remote Similarity	NPD1920	Approved
0.6647	Remote Similarity	NPD2670	Approved
0.6647	Remote Similarity	NPD1919	Approved
0.6634	Remote Similarity	NPD4982	Discontinued
0.6634	Remote Similarity	NPD3947	Discontinued
0.6626	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2509	Approved
0.6618	Remote Similarity	NPD2510	Approved
0.6616	Remote Similarity	NPD3828	Approved
0.6614	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1109	Approved
0.6608	Remote Similarity	NPD1110	Approved
0.6608	Remote Similarity	NPD3170	Approved
0.6607	Remote Similarity	NPD1541	Approved
0.6602	Remote Similarity	NPD5475	Discontinued
0.66	Remote Similarity	NPD6805	Discontinued
0.6596	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6768	Approved
0.6588	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7570	Approved
0.6582	Remote Similarity	NPD7569	Approved
0.6579	Remote Similarity	NPD4330	Approved
0.6579	Remote Similarity	NPD4329	Approved
0.6579	Remote Similarity	NPD3989	Phase 3
0.6578	Remote Similarity	NPD5997	Discontinued
0.6576	Remote Similarity	NPD7036	Phase 3
0.6576	Remote Similarity	NPD7035	Approved
0.6573	Remote Similarity	NPD1230	Approved
0.6571	Remote Similarity	NPD6017	Discontinued
0.6566	Remote Similarity	NPD3964	Approved
0.6561	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1175	Approved
0.6556	Remote Similarity	NPD7072	Phase 2
0.6554	Remote Similarity	NPD7528	Approved
0.6554	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5024	Approved
0.6545	Remote Similarity	NPD3990	Phase 3
0.6543	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5466	Approved
0.654	Remote Similarity	NPD6770	Approved
0.6538	Remote Similarity	NPD7599	Phase 2
0.6529	Remote Similarity	NPD1228	Phase 2
0.6524	Remote Similarity	NPD3776	Discontinued
0.6519	Remote Similarity	NPD6571	Approved
0.6519	Remote Similarity	NPD6570	Approved
0.6517	Remote Similarity	NPD5748	Phase 2
0.6508	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2037	Approved
0.6502	Remote Similarity	NPD6176	Phase 1
0.6494	Remote Similarity	NPD6566	Discontinued
0.6491	Remote Similarity	NPD1207	Approved
0.6491	Remote Similarity	NPD1206	Approved
0.648	Remote Similarity	NPD4499	Approved
0.6477	Remote Similarity	NPD5933	Phase 3
0.6477	Remote Similarity	NPD5932	Phase 3
0.6477	Remote Similarity	NPD5931	Phase 3
0.6467	Remote Similarity	NPD4549	Discontinued
0.6461	Remote Similarity	NPD4942	Approved
0.6458	Remote Similarity	NPD2287	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7572	Phase 2
0.645	Remote Similarity	NPD5003	Discontinued
0.6447	Remote Similarity	NPD8240	Discontinued
0.6447	Remote Similarity	NPD5504	Discontinued
0.6447	Remote Similarity	NPD6659	Phase 2
0.6444	Remote Similarity	NPD1879	Approved
0.6436	Remote Similarity	NPD2431	Approved
0.6436	Remote Similarity	NPD2432	Approved
0.6433	Remote Similarity	NPD2331	Discontinued
0.6429	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5293	Phase 2
0.6429	Remote Similarity	NPD951	Approved
0.6429	Remote Similarity	NPD1208	Approved
0.6425	Remote Similarity	NPD4506	Discontinued
0.6412	Remote Similarity	NPD2949	Approved
0.6412	Remote Similarity	NPD2950	Approved
0.6406	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6238	Discontinued
0.6402	Remote Similarity	NPD4178	Approved
0.6402	Remote Similarity	NPD4176	Approved
0.64	Remote Similarity	NPD5411	Discontinued
0.6398	Remote Similarity	NPD3389	Approved
0.6398	Remote Similarity	NPD3394	Approved
0.6398	Remote Similarity	NPD3393	Approved
0.6387	Remote Similarity	NPD3996	Approved
0.6387	Remote Similarity	NPD3994	Approved
0.6387	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3991	Approved
0.6387	Remote Similarity	NPD3993	Approved
0.6387	Remote Similarity	NPD3995	Approved
0.6387	Remote Similarity	NPD3992	Approved
0.6383	Remote Similarity	NPD7795	Phase 2
0.6379	Remote Similarity	NPD1205	Approved
0.6379	Remote Similarity	NPD1209	Approved
0.6378	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6891	Phase 2
0.6374	Remote Similarity	NPD1531	Approved
0.6373	Remote Similarity	NPD1966	Approved
0.6369	Remote Similarity	NPD979	Approved
0.6364	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6557	Phase 2
0.6359	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3437	Discontinued
0.6354	Remote Similarity	NPD3997	Approved
0.6354	Remote Similarity	NPD3999	Approved
0.6354	Remote Similarity	NPD3998	Approved
0.6354	Remote Similarity	NPD3782	Discontinued
0.6354	Remote Similarity	NPD1854	Approved
0.6354	Remote Similarity	NPD7881	Approved
0.6348	Remote Similarity	NPD4041	Approved
0.6348	Remote Similarity	NPD1524	Phase 1
0.6347	Remote Similarity	NPD552	Approved
0.6347	Remote Similarity	NPD6199	Discontinued
0.6347	Remote Similarity	NPD1593	Approved
0.6347	Remote Similarity	NPD9567	Approved
0.6347	Remote Similarity	NPD553	Approved
0.6343	Remote Similarity	NPD2010	Phase 3
0.6341	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD2672	Discontinued
0.6338	Remote Similarity	NPD7878	Phase 2
0.6335	Remote Similarity	NPD4091	Approved
0.633	Remote Similarity	NPD6457	Approved
0.633	Remote Similarity	NPD2455	Approved
0.633	Remote Similarity	NPD2454	Approved
0.6328	Remote Similarity	NPD2387	Approved
0.6326	Remote Similarity	NPD4301	Approved
0.6325	Remote Similarity	NPD9539	Approved
0.6325	Remote Similarity	NPD9541	Approved
0.6324	Remote Similarity	NPD5552	Discontinued
0.6324	Remote Similarity	NPD6321	Discontinued
0.6324	Remote Similarity	NPD2506	Approved
0.6324	Remote Similarity	NPD7600	Phase 2
0.6313	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD212	Discontinued
0.6302	Remote Similarity	NPD5498	Phase 2
0.6302	Remote Similarity	NPD4092	Approved
0.6302	Remote Similarity	NPD5600	Discontinued
0.63	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2369	Discontinued
0.6296	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4948	Discontinued
0.6294	Remote Similarity	NPD4515	Suspended
0.6292	Remote Similarity	NPD6185	Discontinued
0.6291	Remote Similarity	NPD6218	Discontinued
0.629	Remote Similarity	NPD1210	Approved
0.6289	Remote Similarity	NPD3471	Approved
0.6289	Remote Similarity	NPD3470	Approved
0.6287	Remote Similarity	NPD5515	Phase 2
0.6284	Remote Similarity	NPD7186	Phase 3
0.6283	Remote Similarity	NPD7940	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