NPASS Compound

Structure

NPC473815 OpenBabel07101718222D 24 27 0 0 1 0 0 0 0 0999 V2000 -2.0215 4.6036 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 -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 -1.6942 1.9781 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 -1.4863 2.9563 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 3 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 -0.5352 3.2653 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 -0.7431 2.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2294 3.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 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 14 2 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.1
Volume:	319.085
LogP:	1.246
LogD:	1.333
LogS:	-3.824
# Rotatable Bonds:	3
TPSA:	81.42
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	2.899
Fsp3:	0.167
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:	-4.808
MDCK Permeability:	2.618569487822242e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.931
Plasma Protein Binding (PPB):	64.31331634521484%
Volume Distribution (VD):	0.646
Pgp-substrate:	16.15067481994629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.249
CYP2C9-substrate:	0.652
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	1.464
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.481
Drug-inuced Liver Injury (DILI):	0.327
AMES Toxicity:	0.665
Rat Oral Acute Toxicity:	0.49
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.095
Carcinogencity:	0.787
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.691

Download Data

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

Natural Product: NPC473815

Natural Product ID:	NPC473815
*Common Name:**	Phaitanthrins B
IUPAC Name:	methyl 2-(6-hydroxy-12-oxoindolo[2,1-b]quinazolin-6-yl)acetate
Synonyms:	phaitanthrins B
Standard InCHIKey:	CGMNLIDQBYRXFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14N2O4/c1-24-15(21)10-18(23)12-7-3-5-9-14(12)20-16(22)11-6-2-4-8-13(11)19-17(18)20/h2-9,23H,10H2,1H3
SMILES:	COC(=O)CC1(O)c2nc3ccccc3c(=O)n2c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452546
PubChem CID:	24970643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines [CHEMONTID:0002087] Indoloquinazolines

*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[505862]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[505862]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[505862]

☑ 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 NPC473815 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	386
0.1-0.2	2694
0.2-0.3	12763
0.3-0.4	13276
0.4-0.5	9323
0.5-0.6	2888
0.6-0.7	1191
0.7-0.8	139
0.8-0.85	31
0.85-0.9	0
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9281	High Similarity	NPC475594
0.9226	High Similarity	NPC475607
0.9172	High Similarity	NPC474081
0.9006	High Similarity	NPC474041
0.9006	High Similarity	NPC475761
0.8629	High Similarity	NPC475685
0.8087	Intermediate Similarity	NPC150308
0.7889	Intermediate Similarity	NPC470548
0.7861	Intermediate Similarity	NPC471196
0.7861	Intermediate Similarity	NPC471195
0.7853	Intermediate Similarity	NPC471130
0.7842	Intermediate Similarity	NPC470787
0.7842	Intermediate Similarity	NPC472539
0.7842	Intermediate Similarity	NPC472540
0.7841	Intermediate Similarity	NPC88970
0.7835	Intermediate Similarity	NPC295548
0.7806	Intermediate Similarity	NPC470786
0.7801	Intermediate Similarity	NPC472542
0.7801	Intermediate Similarity	NPC472541
0.7755	Intermediate Similarity	NPC225400
0.7723	Intermediate Similarity	NPC244425
0.7723	Intermediate Similarity	NPC15384
0.7716	Intermediate Similarity	NPC471155
0.7716	Intermediate Similarity	NPC472538
0.7677	Intermediate Similarity	NPC270241
0.7635	Intermediate Similarity	NPC471197
0.7598	Intermediate Similarity	NPC471198
0.7542	Intermediate Similarity	NPC476231
0.7515	Intermediate Similarity	NPC207554
0.75	Intermediate Similarity	NPC285192
0.7446	Intermediate Similarity	NPC177261
0.7427	Intermediate Similarity	NPC248601
0.7389	Intermediate Similarity	NPC27904
0.7358	Intermediate Similarity	NPC92803
0.7356	Intermediate Similarity	NPC324445
0.7344	Intermediate Similarity	NPC18890
0.7278	Intermediate Similarity	NPC300299
0.7264	Intermediate Similarity	NPC314648
0.7228	Intermediate Similarity	NPC182131
0.7213	Intermediate Similarity	NPC189116
0.7192	Intermediate Similarity	NPC243850
0.7175	Intermediate Similarity	NPC300596
0.7175	Intermediate Similarity	NPC237649
0.7172	Intermediate Similarity	NPC471199
0.7151	Intermediate Similarity	NPC83214
0.7143	Intermediate Similarity	NPC313796
0.7143	Intermediate Similarity	NPC313345
0.7143	Intermediate Similarity	NPC154478
0.7143	Intermediate Similarity	NPC315638
0.7143	Intermediate Similarity	NPC314855
0.7135	Intermediate Similarity	NPC472115
0.7135	Intermediate Similarity	NPC472114
0.7112	Intermediate Similarity	NPC355
0.7111	Intermediate Similarity	NPC295021
0.7108	Intermediate Similarity	NPC315545
0.7108	Intermediate Similarity	NPC314297
0.71	Intermediate Similarity	NPC106118
0.7087	Intermediate Similarity	NPC314834
0.7081	Intermediate Similarity	NPC471124
0.7077	Intermediate Similarity	NPC221873
0.7071	Intermediate Similarity	NPC198401
0.7047	Intermediate Similarity	NPC471742
0.7039	Intermediate Similarity	NPC144691
0.703	Intermediate Similarity	NPC471944
0.7027	Intermediate Similarity	NPC313757
0.7021	Intermediate Similarity	NPC318183
0.701	Intermediate Similarity	NPC322621
0.7	Intermediate Similarity	NPC129624
0.6995	Remote Similarity	NPC211525
0.6995	Remote Similarity	NPC153694
0.6974	Remote Similarity	NPC282092
0.6957	Remote Similarity	NPC471122
0.6952	Remote Similarity	NPC278887
0.6941	Remote Similarity	NPC314098
0.6941	Remote Similarity	NPC316746
0.694	Remote Similarity	NPC84317
0.6935	Remote Similarity	NPC204867
0.6923	Remote Similarity	NPC471132
0.6914	Remote Similarity	NPC242933
0.6901	Remote Similarity	NPC207428
0.6898	Remote Similarity	NPC470069
0.6898	Remote Similarity	NPC52059
0.6875	Remote Similarity	NPC43477
0.6866	Remote Similarity	NPC97100
0.6866	Remote Similarity	NPC473375
0.6865	Remote Similarity	NPC310403
0.6865	Remote Similarity	NPC97380
0.6865	Remote Similarity	NPC243673
0.6865	Remote Similarity	NPC63210
0.6865	Remote Similarity	NPC263709
0.6865	Remote Similarity	NPC148468
0.686	Remote Similarity	NPC16249
0.6845	Remote Similarity	NPC113056
0.6845	Remote Similarity	NPC138293
0.6839	Remote Similarity	NPC475094
0.6839	Remote Similarity	NPC321211
0.6823	Remote Similarity	NPC471743
0.6821	Remote Similarity	NPC253476
0.6821	Remote Similarity	NPC470317
0.6812	Remote Similarity	NPC471191
0.6806	Remote Similarity	NPC298851
0.6806	Remote Similarity	NPC181138
0.6806	Remote Similarity	NPC210415
0.6806	Remote Similarity	NPC220851
0.6806	Remote Similarity	NPC21752
0.6806	Remote Similarity	NPC276993
0.6806	Remote Similarity	NPC293255
0.68	Remote Similarity	NPC122553
0.6791	Remote Similarity	NPC293458
0.6791	Remote Similarity	NPC472117
0.6786	Remote Similarity	NPC245741
0.6786	Remote Similarity	NPC203635
0.6786	Remote Similarity	NPC97584
0.6784	Remote Similarity	NPC5630
0.678	Remote Similarity	NPC2823
0.6771	Remote Similarity	NPC13367
0.676	Remote Similarity	NPC314186
0.675	Remote Similarity	NPC203628
0.6746	Remote Similarity	NPC205946
0.6736	Remote Similarity	NPC84347
0.6735	Remote Similarity	NPC243058
0.672	Remote Similarity	NPC123241
0.6717	Remote Similarity	NPC90415
0.6715	Remote Similarity	NPC165599
0.6715	Remote Similarity	NPC317572
0.6704	Remote Similarity	NPC308197
0.6703	Remote Similarity	NPC161827
0.6702	Remote Similarity	NPC199737
0.6701	Remote Similarity	NPC14849
0.6701	Remote Similarity	NPC285923
0.67	Remote Similarity	NPC313293
0.6699	Remote Similarity	NPC244741
0.6686	Remote Similarity	NPC226662
0.6685	Remote Similarity	NPC478039
0.6685	Remote Similarity	NPC259678
0.6684	Remote Similarity	NPC36495
0.6682	Remote Similarity	NPC157931
0.6667	Remote Similarity	NPC131450
0.6667	Remote Similarity	NPC29285
0.6667	Remote Similarity	NPC256268
0.6667	Remote Similarity	NPC147298
0.6667	Remote Similarity	NPC182057
0.6667	Remote Similarity	NPC141454
0.6667	Remote Similarity	NPC89508
0.6652	Remote Similarity	NPC471762
0.6651	Remote Similarity	NPC312645
0.665	Remote Similarity	NPC221687
0.665	Remote Similarity	NPC477159
0.6649	Remote Similarity	NPC143457
0.6649	Remote Similarity	NPC476441
0.6633	Remote Similarity	NPC298320
0.6633	Remote Similarity	NPC291759
0.6633	Remote Similarity	NPC39822
0.6632	Remote Similarity	NPC299582
0.6629	Remote Similarity	NPC472243
0.6628	Remote Similarity	NPC197680
0.6628	Remote Similarity	NPC259098
0.662	Remote Similarity	NPC6865
0.662	Remote Similarity	NPC153980
0.662	Remote Similarity	NPC127996
0.6619	Remote Similarity	NPC478075
0.6618	Remote Similarity	NPC303214
0.6618	Remote Similarity	NPC232600
0.6617	Remote Similarity	NPC45389
0.6615	Remote Similarity	NPC219848
0.6615	Remote Similarity	NPC469915
0.6615	Remote Similarity	NPC472118
0.6615	Remote Similarity	NPC186669
0.6612	Remote Similarity	NPC242000
0.6605	Remote Similarity	NPC471192
0.6603	Remote Similarity	NPC132539
0.6599	Remote Similarity	NPC475962
0.6598	Remote Similarity	NPC248862
0.6598	Remote Similarity	NPC328611
0.6597	Remote Similarity	NPC214960
0.6597	Remote Similarity	NPC279527
0.6591	Remote Similarity	NPC173295
0.659	Remote Similarity	NPC194562
0.6587	Remote Similarity	NPC57398
0.6584	Remote Similarity	NPC28510
0.6583	Remote Similarity	NPC52262
0.6583	Remote Similarity	NPC133591
0.658	Remote Similarity	NPC292265
0.6577	Remote Similarity	NPC66777
0.6573	Remote Similarity	NPC72956
0.6573	Remote Similarity	NPC181527
0.6569	Remote Similarity	NPC476205
0.6569	Remote Similarity	NPC476129
0.6569	Remote Similarity	NPC476206
0.6569	Remote Similarity	NPC476207
0.6569	Remote Similarity	NPC476212
0.6569	Remote Similarity	NPC476257
0.6569	Remote Similarity	NPC259791
0.6569	Remote Similarity	NPC476256
0.6569	Remote Similarity	NPC202812
0.6561	Remote Similarity	NPC474058
0.6561	Remote Similarity	NPC225319
0.6561	Remote Similarity	NPC93653
0.6553	Remote Similarity	NPC474916
0.655	Remote Similarity	NPC207033

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 NPC473815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	619
0.2-0.3	914
0.3-0.4	1721
0.4-0.5	2690
0.5-0.6	2030
0.6-0.7	832
0.7-0.8	96
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
0.768	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5042	Phase 1
0.7398	Intermediate Similarity	NPD5856	Discontinued
0.7316	Intermediate Similarity	NPD5923	Phase 1
0.7305	Intermediate Similarity	NPD1919	Approved
0.7305	Intermediate Similarity	NPD1920	Approved
0.7232	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4412	Phase 2
0.7188	Intermediate Similarity	NPD6557	Phase 2
0.7113	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6017	Discontinued
0.7088	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1625	Approved
0.7085	Intermediate Similarity	NPD5515	Phase 2
0.7079	Intermediate Similarity	NPD4888	Discontinued
0.7059	Intermediate Similarity	NPD6260	Discontinued
0.7044	Intermediate Similarity	NPD3802	Phase 3
0.7029	Intermediate Similarity	NPD2365	Approved
0.7026	Intermediate Similarity	NPD4515	Suspended
0.6989	Remote Similarity	NPD2820	Phase 3
0.6989	Remote Similarity	NPD5430	Discontinued
0.6983	Remote Similarity	NPD4161	Discontinued
0.6983	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2791	Discontinued
0.6934	Remote Similarity	NPD7878	Phase 2
0.6931	Remote Similarity	NPD3776	Discontinued
0.6919	Remote Similarity	NPD2506	Approved
0.6911	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4430	Phase 2
0.6891	Remote Similarity	NPD5445	Approved
0.6884	Remote Similarity	NPD7570	Approved
0.6884	Remote Similarity	NPD7569	Approved
0.6884	Remote Similarity	NPD8146	Phase 2
0.6881	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7186	Phase 3
0.6857	Remote Similarity	NPD1626	Approved
0.6845	Remote Similarity	NPD3947	Discontinued
0.6839	Remote Similarity	NPD3782	Discontinued
0.6836	Remote Similarity	NPD1189	Approved
0.6834	Remote Similarity	NPD2336	Approved
0.6832	Remote Similarity	NPD5003	Discontinued
0.683	Remote Similarity	NPD7560	Approved
0.6828	Remote Similarity	NPD4311	Approved
0.6818	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6805	Discontinued
0.6812	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD212	Discontinued
0.6809	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4330	Approved
0.6804	Remote Similarity	NPD4329	Approved
0.68	Remote Similarity	NPD5937	Approved
0.6796	Remote Similarity	NPD7205	Discontinued
0.6796	Remote Similarity	NPD4942	Approved
0.6788	Remote Similarity	NPD3792	Approved
0.6788	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2427	Approved
0.6773	Remote Similarity	NPD6199	Discontinued
0.6771	Remote Similarity	NPD3423	Phase 2
0.6771	Remote Similarity	NPD3422	Phase 3
0.6771	Remote Similarity	NPD5466	Approved
0.6769	Remote Similarity	NPD3990	Phase 3
0.6768	Remote Similarity	NPD4948	Discontinued
0.6762	Remote Similarity	NPD5860	Discontinued
0.6761	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5504	Discontinued
0.6746	Remote Similarity	NPD6486	Approved
0.6746	Remote Similarity	NPD7232	Discontinued
0.6746	Remote Similarity	NPD6487	Approved
0.6739	Remote Similarity	NPD5086	Approved
0.6737	Remote Similarity	NPD2037	Approved
0.6734	Remote Similarity	NPD4334	Discontinued
0.673	Remote Similarity	NPD4493	Discontinued
0.6729	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7011	Discontinued
0.6718	Remote Similarity	NPD3989	Phase 3
0.6703	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD721	Approved
0.6701	Remote Similarity	NPD4092	Approved
0.67	Remote Similarity	NPD2565	Phase 2
0.67	Remote Similarity	NPD2564	Approved
0.67	Remote Similarity	NPD2307	Discontinued
0.67	Remote Similarity	NPD5411	Discontinued
0.6698	Remote Similarity	NPD7225	Discontinued
0.6685	Remote Similarity	NPD1524	Phase 1
0.6682	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2387	Approved
0.6667	Remote Similarity	NPD1541	Approved
0.6667	Remote Similarity	NPD3774	Approved
0.6667	Remote Similarity	NPD3773	Approved
0.6667	Remote Similarity	NPD7552	Discontinued
0.6667	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3775	Approved
0.6667	Remote Similarity	NPD5077	Approved
0.6667	Remote Similarity	NPD5076	Approved
0.6667	Remote Similarity	NPD3780	Phase 2
0.6667	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD3997	Approved
0.6667	Remote Similarity	NPD3998	Approved
0.6667	Remote Similarity	NPD3999	Approved
0.665	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2404	Discontinued
0.6649	Remote Similarity	NPD4091	Approved
0.6648	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3377	Discontinued
0.663	Remote Similarity	NPD1230	Approved
0.6615	Remote Similarity	NPD3991	Approved
0.6615	Remote Similarity	NPD3994	Approved
0.6615	Remote Similarity	NPD3993	Approved
0.6615	Remote Similarity	NPD3996	Approved
0.6615	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3992	Approved
0.6615	Remote Similarity	NPD3995	Approved
0.661	Remote Similarity	NPD2670	Approved
0.6603	Remote Similarity	NPD5901	Discontinued
0.6602	Remote Similarity	NPD6874	Approved
0.66	Remote Similarity	NPD6891	Phase 2
0.6598	Remote Similarity	NPD2359	Approved
0.6598	Remote Similarity	NPD3522	Approved
0.6596	Remote Similarity	NPD7599	Phase 2
0.659	Remote Similarity	NPD3258	Approved
0.6588	Remote Similarity	NPD4082	Approved
0.6585	Remote Similarity	NPD3828	Approved
0.6584	Remote Similarity	NPD4370	Phase 3
0.6584	Remote Similarity	NPD6659	Phase 2
0.6582	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.658	Remote Similarity	NPD2431	Approved
0.658	Remote Similarity	NPD2432	Approved
0.6578	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD2836	Approved
0.6578	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6142	Phase 3
0.6578	Remote Similarity	NPD6395	Phase 2
0.6578	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1527	Phase 2
0.6571	Remote Similarity	NPD7001	Phase 3
0.6566	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4938	Phase 2
0.6564	Remote Similarity	NPD2361	Approved
0.6564	Remote Similarity	NPD7677	Discontinued
0.6562	Remote Similarity	NPD2455	Approved
0.6562	Remote Similarity	NPD2454	Approved
0.6557	Remote Similarity	NPD5593	Approved
0.6557	Remote Similarity	NPD1801	Approved
0.6557	Remote Similarity	NPD1802	Approved
0.6557	Remote Similarity	NPD5594	Approved
0.6552	Remote Similarity	NPD4315	Phase 2
0.6548	Remote Similarity	NPD3227	Phase 2
0.6528	Remote Similarity	NPD7795	Phase 2
0.6528	Remote Similarity	NPD7167	Discontinued
0.6526	Remote Similarity	NPD3893	Discontinued
0.6524	Remote Similarity	NPD7072	Phase 2
0.6524	Remote Similarity	NPD6987	Phase 1
0.6522	Remote Similarity	NPD979	Approved
0.6522	Remote Similarity	NPD4946	Phase 2
0.652	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3471	Approved
0.6515	Remote Similarity	NPD3470	Approved
0.6514	Remote Similarity	NPD5496	Approved
0.6513	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD956	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9477	Approved
0.6498	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD683	Approved
0.6488	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5748	Phase 2
0.6481	Remote Similarity	NPD3257	Approved
0.648	Remote Similarity	NPD700	Approved
0.648	Remote Similarity	NPD13	Approved
0.648	Remote Similarity	NPD697	Approved
0.648	Remote Similarity	NPD12	Approved
0.648	Remote Similarity	NPD699	Approved
0.6477	Remote Similarity	NPD1595	Approved
0.6477	Remote Similarity	NPD2844	Phase 3
0.6477	Remote Similarity	NPD1594	Phase 3
0.6477	Remote Similarity	NPD6457	Approved
0.6474	Remote Similarity	NPD7600	Phase 2
0.6473	Remote Similarity	NPD7778	Approved
0.6473	Remote Similarity	NPD7777	Approved
0.6473	Remote Similarity	NPD53	Approved
0.6471	Remote Similarity	NPD3229	Phase 2
0.6465	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4492	Approved
0.6465	Remote Similarity	NPD6878	Phase 2
0.6465	Remote Similarity	NPD3918	Approved
0.6465	Remote Similarity	NPD3917	Approved
0.6465	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4494	Approved
0.6465	Remote Similarity	NPD6879	Phase 2
0.6462	Remote Similarity	NPD6518	Discontinued
0.6457	Remote Similarity	NPD6292	Clinical (unspecified phase)

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