NPASS Compound

Structure

NPC103119 OpenBabel07101718292D 23 26 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 -0.8759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4369 -0.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8576 -1.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7424 0.2272 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -0.9757 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -0.2070 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 0.8660 -1.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 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 -0.8660 0.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 10 2 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.09
Volume:	322.22
LogP:	3.18
LogD:	2.745
LogS:	-4.138
# Rotatable Bonds:	2
TPSA:	72.03
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	3.102
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134
MDCK Permeability:	4.498232101468602e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.311
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	96.27637481689453%
Volume Distribution (VD):	0.814
Pgp-substrate:	2.2482731342315674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.416
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.185
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.819
CYP3A4-inhibitor:	0.356
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	3.379
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.902
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.85
Carcinogencity:	0.526
Eye Corrosion:	0.011
Eye Irritation:	0.078
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: NPC103119

Natural Product ID:	NPC103119
*Common Name:**	Diplamine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KEDRDGVCNOXHKD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15N3OS/c1-23-18-12(6-8-19)15-14-11(7-9-20-16(14)17(18)22)10-4-2-3-5-13(10)21-15/h2-5,7,9H,6,8,19H2,1H3
SMILES:	CSC1=C(CCN)c2c3c(ccnc3C1=O)c1ccccc1n2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513108
PubChem CID:	44588491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0001810] Pyridoacridones [CHEMONTID:0002826] Pyrido[2,3,4-kl]acridones

*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
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17269824]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18977148]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28181805]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3728	Individual Protein	p53-binding protein Mdm-2	Homo sapiens	IC50	=	101300.0	nM	PMID[571451]

☑ 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 NPC103119 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	543
0.1-0.2	6211
0.2-0.3	15750
0.3-0.4	14266
0.4-0.5	2229
0.5-0.6	2166
0.6-0.7	1269
0.7-0.8	248
0.8-0.85	11
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9532	High Similarity	NPC255909
0.9118	High Similarity	NPC157583
0.8678	High Similarity	NPC237188
0.8516	High Similarity	NPC216550
0.8413	Intermediate Similarity	NPC88115
0.8404	Intermediate Similarity	NPC106757
0.8387	Intermediate Similarity	NPC34837
0.8333	Intermediate Similarity	NPC467063
0.8235	Intermediate Similarity	NPC167710
0.8115	Intermediate Similarity	NPC328318
0.8115	Intermediate Similarity	NPC328596
0.8031	Intermediate Similarity	NPC327592
0.8022	Intermediate Similarity	NPC191415
0.799	Intermediate Similarity	NPC317373
0.7989	Intermediate Similarity	NPC128244
0.7884	Intermediate Similarity	NPC326422
0.7857	Intermediate Similarity	NPC284775
0.7806	Intermediate Similarity	NPC472064
0.775	Intermediate Similarity	NPC318299
0.7737	Intermediate Similarity	NPC272458
0.7722	Intermediate Similarity	NPC70949
0.7716	Intermediate Similarity	NPC472065
0.7711	Intermediate Similarity	NPC317752
0.7696	Intermediate Similarity	NPC304203
0.7688	Intermediate Similarity	NPC102755
0.7684	Intermediate Similarity	NPC80681
0.766	Intermediate Similarity	NPC118084
0.7647	Intermediate Similarity	NPC477003
0.7644	Intermediate Similarity	NPC473878
0.76	Intermediate Similarity	NPC70406
0.7592	Intermediate Similarity	NPC476460
0.759	Intermediate Similarity	NPC284338
0.7582	Intermediate Similarity	NPC91895
0.7577	Intermediate Similarity	NPC106824
0.7563	Intermediate Similarity	NPC472062
0.7563	Intermediate Similarity	NPC472063
0.7563	Intermediate Similarity	NPC472069
0.7557	Intermediate Similarity	NPC251391
0.7556	Intermediate Similarity	NPC265100
0.7539	Intermediate Similarity	NPC268966
0.7526	Intermediate Similarity	NPC477415
0.7526	Intermediate Similarity	NPC23476
0.7526	Intermediate Similarity	NPC474259
0.7525	Intermediate Similarity	NPC317701
0.7514	Intermediate Similarity	NPC467188
0.75	Intermediate Similarity	NPC237740
0.75	Intermediate Similarity	NPC237414
0.7486	Intermediate Similarity	NPC474492
0.7474	Intermediate Similarity	NPC469359
0.7473	Intermediate Similarity	NPC56233
0.7461	Intermediate Similarity	NPC47190
0.7444	Intermediate Similarity	NPC470680
0.7444	Intermediate Similarity	NPC100104
0.7429	Intermediate Similarity	NPC105811
0.7418	Intermediate Similarity	NPC115232
0.7418	Intermediate Similarity	NPC42372
0.7405	Intermediate Similarity	NPC252572
0.7401	Intermediate Similarity	NPC470679
0.7401	Intermediate Similarity	NPC217021
0.7386	Intermediate Similarity	NPC123906
0.7366	Intermediate Similarity	NPC293216
0.7363	Intermediate Similarity	NPC21174
0.7363	Intermediate Similarity	NPC271797
0.7358	Intermediate Similarity	NPC324091
0.7351	Intermediate Similarity	NPC262338
0.7345	Intermediate Similarity	NPC313889
0.734	Intermediate Similarity	NPC472070
0.733	Intermediate Similarity	NPC133003
0.731	Intermediate Similarity	NPC227582
0.731	Intermediate Similarity	NPC314102
0.731	Intermediate Similarity	NPC251722
0.7308	Intermediate Similarity	NPC242116
0.7303	Intermediate Similarity	NPC216713
0.7302	Intermediate Similarity	NPC73994
0.7302	Intermediate Similarity	NPC477042
0.7268	Intermediate Similarity	NPC478184
0.7258	Intermediate Similarity	NPC201634
0.7251	Intermediate Similarity	NPC216612
0.7245	Intermediate Similarity	NPC477414
0.7245	Intermediate Similarity	NPC225622
0.7245	Intermediate Similarity	NPC221726
0.724	Intermediate Similarity	NPC99939
0.724	Intermediate Similarity	NPC308931
0.7236	Intermediate Similarity	NPC74413
0.7236	Intermediate Similarity	NPC81535
0.7234	Intermediate Similarity	NPC151635
0.7233	Intermediate Similarity	NPC477413
0.7232	Intermediate Similarity	NPC471957
0.7232	Intermediate Similarity	NPC100726
0.7222	Intermediate Similarity	NPC209362
0.7217	Intermediate Similarity	NPC322482
0.7208	Intermediate Similarity	NPC294693
0.7207	Intermediate Similarity	NPC470823
0.7206	Intermediate Similarity	NPC116555
0.7202	Intermediate Similarity	NPC135601
0.7202	Intermediate Similarity	NPC141612
0.7202	Intermediate Similarity	NPC17273
0.72	Intermediate Similarity	NPC252338
0.7189	Intermediate Similarity	NPC114637
0.7177	Intermediate Similarity	NPC469727
0.7174	Intermediate Similarity	NPC478182
0.7173	Intermediate Similarity	NPC470677
0.7172	Intermediate Similarity	NPC102592
0.7172	Intermediate Similarity	NPC79356
0.7167	Intermediate Similarity	NPC200214
0.7157	Intermediate Similarity	NPC175916
0.7151	Intermediate Similarity	NPC471655
0.7151	Intermediate Similarity	NPC40070
0.715	Intermediate Similarity	NPC477004
0.7143	Intermediate Similarity	NPC213914
0.7129	Intermediate Similarity	NPC260900
0.7127	Intermediate Similarity	NPC229055
0.7122	Intermediate Similarity	NPC66699
0.7121	Intermediate Similarity	NPC157828
0.7121	Intermediate Similarity	NPC195239
0.712	Intermediate Similarity	NPC182940
0.712	Intermediate Similarity	NPC79777
0.7119	Intermediate Similarity	NPC86288
0.7111	Intermediate Similarity	NPC470233
0.7104	Intermediate Similarity	NPC293487
0.7103	Intermediate Similarity	NPC19170
0.7102	Intermediate Similarity	NPC190296
0.71	Intermediate Similarity	NPC476143
0.7095	Intermediate Similarity	NPC267811
0.7095	Intermediate Similarity	NPC321911
0.709	Intermediate Similarity	NPC139763
0.7088	Intermediate Similarity	NPC74357
0.7085	Intermediate Similarity	NPC11445
0.7081	Intermediate Similarity	NPC274981
0.7081	Intermediate Similarity	NPC317105
0.7072	Intermediate Similarity	NPC325903
0.7069	Intermediate Similarity	NPC169433
0.7065	Intermediate Similarity	NPC44773
0.7065	Intermediate Similarity	NPC215584
0.705	Intermediate Similarity	NPC272483
0.7047	Intermediate Similarity	NPC470205
0.7039	Intermediate Similarity	NPC469811
0.7039	Intermediate Similarity	NPC179787
0.7039	Intermediate Similarity	NPC201380
0.7037	Intermediate Similarity	NPC161861
0.7031	Intermediate Similarity	NPC234403
0.7029	Intermediate Similarity	NPC110126
0.7027	Intermediate Similarity	NPC194881
0.7022	Intermediate Similarity	NPC314372
0.7022	Intermediate Similarity	NPC285731
0.7019	Intermediate Similarity	NPC124636
0.7016	Intermediate Similarity	NPC14113
0.7016	Intermediate Similarity	NPC83774
0.7016	Intermediate Similarity	NPC145885
0.7016	Intermediate Similarity	NPC248454
0.7016	Intermediate Similarity	NPC84827
0.7011	Intermediate Similarity	NPC56765
0.7011	Intermediate Similarity	NPC84911
0.7011	Intermediate Similarity	NPC105127
0.701	Intermediate Similarity	NPC476252
0.701	Intermediate Similarity	NPC21429
0.7005	Intermediate Similarity	NPC478183
0.7005	Intermediate Similarity	NPC154339
0.7005	Intermediate Similarity	NPC297862
0.7	Intermediate Similarity	NPC472116
0.6989	Remote Similarity	NPC469784
0.6989	Remote Similarity	NPC469768
0.6989	Remote Similarity	NPC469779
0.6989	Remote Similarity	NPC469780
0.6989	Remote Similarity	NPC469767
0.6989	Remote Similarity	NPC469761
0.6989	Remote Similarity	NPC469783
0.6986	Remote Similarity	NPC193370
0.6986	Remote Similarity	NPC470702
0.6986	Remote Similarity	NPC473218
0.6985	Remote Similarity	NPC267343
0.6983	Remote Similarity	NPC63545
0.6983	Remote Similarity	NPC288838
0.6979	Remote Similarity	NPC55772
0.6979	Remote Similarity	NPC213468
0.6979	Remote Similarity	NPC248041
0.6979	Remote Similarity	NPC126709
0.6979	Remote Similarity	NPC11126
0.6978	Remote Similarity	NPC138842
0.6963	Remote Similarity	NPC267885
0.6961	Remote Similarity	NPC105818
0.6961	Remote Similarity	NPC53947
0.6961	Remote Similarity	NPC24678
0.6957	Remote Similarity	NPC266249
0.6957	Remote Similarity	NPC76982
0.6954	Remote Similarity	NPC261195
0.6954	Remote Similarity	NPC96102
0.6954	Remote Similarity	NPC29886
0.6952	Remote Similarity	NPC470703
0.6949	Remote Similarity	NPC469766
0.6946	Remote Similarity	NPC46358
0.6943	Remote Similarity	NPC61011
0.6939	Remote Similarity	NPC62749
0.6935	Remote Similarity	NPC478185
0.6934	Remote Similarity	NPC27041
0.6934	Remote Similarity	NPC173344
0.6932	Remote Similarity	NPC73767
0.6931	Remote Similarity	NPC471943
0.6927	Remote Similarity	NPC159856
0.6923	Remote Similarity	NPC228835

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 NPC103119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	683
0.2-0.3	984
0.3-0.4	2076
0.4-0.5	2209
0.5-0.6	1987
0.6-0.7	835
0.7-0.8	99
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD7564	Discontinued
0.7765	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2720	Phase 1
0.7611	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5473	Discontinued
0.7566	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1270	Approved
0.7526	Intermediate Similarity	NPD7027	Phase 3
0.7487	Intermediate Similarity	NPD2479	Phase 3
0.7487	Intermediate Similarity	NPD2481	Approved
0.7473	Intermediate Similarity	NPD6446	Discontinued
0.7438	Intermediate Similarity	NPD6152	Phase 1
0.7435	Intermediate Similarity	NPD4988	Discontinued
0.7432	Intermediate Similarity	NPD1343	Approved
0.7429	Intermediate Similarity	NPD4547	Phase 3
0.7389	Intermediate Similarity	NPD4051	Discontinued
0.7363	Intermediate Similarity	NPD3583	Phase 2
0.7353	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3610	Approved
0.7351	Intermediate Similarity	NPD3609	Approved
0.7326	Intermediate Similarity	NPD6044	Discontinued
0.7323	Intermediate Similarity	NPD2405	Phase 3
0.7323	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7209	Approved
0.7313	Intermediate Similarity	NPD7207	Approved
0.7313	Intermediate Similarity	NPD7208	Approved
0.731	Intermediate Similarity	NPD5446	Phase 2
0.7292	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2753	Discontinued
0.7286	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2837	Discontinued
0.7259	Intermediate Similarity	NPD4848	Phase 1
0.7249	Intermediate Similarity	NPD3078	Approved
0.7249	Intermediate Similarity	NPD3079	Approved
0.7249	Intermediate Similarity	NPD3076	Approved
0.7249	Intermediate Similarity	NPD3077	Approved
0.7243	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3238	Discontinued
0.7234	Intermediate Similarity	NPD2771	Approved
0.7231	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6771	Discontinued
0.7213	Intermediate Similarity	NPD5400	Approved
0.7213	Intermediate Similarity	NPD5315	Discontinued
0.7213	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6459	Phase 2
0.7198	Intermediate Similarity	NPD5888	Phase 2
0.7188	Intermediate Similarity	NPD6178	Phase 3
0.7172	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2640	Approved
0.7151	Intermediate Similarity	NPD2641	Approved
0.7143	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3394	Approved
0.7129	Intermediate Similarity	NPD3389	Approved
0.7129	Intermediate Similarity	NPD3393	Approved
0.7129	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5198	Approved
0.7109	Intermediate Similarity	NPD5199	Approved
0.7107	Intermediate Similarity	NPD4922	Phase 2
0.7102	Intermediate Similarity	NPD2006	Phase 2
0.71	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2430	Phase 2
0.7083	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD991	Phase 2
0.7081	Intermediate Similarity	NPD3323	Discontinued
0.7073	Intermediate Similarity	NPD3905	Phase 3
0.7056	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4075	Phase 2
0.7053	Intermediate Similarity	NPD3348	Phase 2
0.7052	Intermediate Similarity	NPD1253	Approved
0.7052	Intermediate Similarity	NPD1256	Approved
0.7052	Intermediate Similarity	NPD1254	Approved
0.7052	Intermediate Similarity	NPD1255	Approved
0.7047	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1722	Approved
0.7037	Intermediate Similarity	NPD750	Phase 2
0.7035	Intermediate Similarity	NPD7619	Phase 3
0.7035	Intermediate Similarity	NPD7618	Phase 3
0.7031	Intermediate Similarity	NPD3927	Phase 2
0.7026	Intermediate Similarity	NPD5809	Phase 3
0.7026	Intermediate Similarity	NPD7026	Phase 2
0.7024	Intermediate Similarity	NPD5489	Phase 1
0.7024	Intermediate Similarity	NPD5491	Phase 3
0.7017	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4304	Discovery
0.7005	Intermediate Similarity	NPD5636	Discontinued
0.7	Intermediate Similarity	NPD3100	Discontinued
0.6995	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4913	Phase 3
0.699	Remote Similarity	NPD1506	Discontinued
0.6989	Remote Similarity	NPD1545	Discontinued
0.6986	Remote Similarity	NPD6954	Phase 2
0.6979	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8114	Approved
0.6976	Remote Similarity	NPD8115	Approved
0.6973	Remote Similarity	NPD1404	Approved
0.6973	Remote Similarity	NPD1403	Approved
0.6968	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6664	Approved
0.6963	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2879	Approved
0.6961	Remote Similarity	NPD2881	Approved
0.6959	Remote Similarity	NPD5106	Approved
0.6959	Remote Similarity	NPD5105	Approved
0.6954	Remote Similarity	NPD7175	Phase 1
0.6954	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6787	Phase 2
0.695	Remote Similarity	NPD5855	Phase 3
0.695	Remote Similarity	NPD7406	Phase 2
0.695	Remote Similarity	NPD5853	Phase 3
0.6944	Remote Similarity	NPD1661	Suspended
0.6942	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2008	Discontinued
0.6942	Remote Similarity	NPD7010	Phase 3
0.694	Remote Similarity	NPD2165	Phase 1
0.6936	Remote Similarity	NPD3942	Approved
0.6936	Remote Similarity	NPD3944	Approved
0.6935	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5505	Discontinued
0.6934	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD786	Approved
0.6931	Remote Similarity	NPD1982	Phase 1
0.6923	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9583	Approved
0.6919	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2639	Approved
0.6915	Remote Similarity	NPD2642	Approved
0.6912	Remote Similarity	NPD8289	Discontinued
0.6911	Remote Similarity	NPD482	Approved
0.6911	Remote Similarity	NPD4883	Approved
0.691	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2411	Approved
0.6904	Remote Similarity	NPD3961	Discontinued
0.6904	Remote Similarity	NPD7394	Phase 2
0.6902	Remote Similarity	NPD3115	Approved
0.6902	Remote Similarity	NPD3114	Approved
0.6902	Remote Similarity	NPD3113	Approved
0.6902	Remote Similarity	NPD3112	Approved
0.6901	Remote Similarity	NPD947	Approved
0.6897	Remote Similarity	NPD6239	Discontinued
0.6893	Remote Similarity	NPD5901	Discontinued
0.6893	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7469	Discontinued
0.6888	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2336	Approved
0.6882	Remote Similarity	NPD2118	Approved
0.6882	Remote Similarity	NPD2119	Approved
0.6878	Remote Similarity	NPD7187	Phase 2
0.6878	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7666	Phase 3
0.6875	Remote Similarity	NPD2509	Approved
0.6875	Remote Similarity	NPD7665	Phase 2
0.6875	Remote Similarity	NPD2510	Approved
0.6872	Remote Similarity	NPD3319	Phase 1
0.6872	Remote Similarity	NPD4509	Discontinued
0.6872	Remote Similarity	NPD3794	Approved
0.6872	Remote Similarity	NPD3320	Approved
0.6872	Remote Similarity	NPD3318	Approved
0.6872	Remote Similarity	NPD3795	Approved
0.6868	Remote Similarity	NPD2172	Phase 1
0.6865	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6479	Discontinued
0.686	Remote Similarity	NPD715	Phase 3
0.685	Remote Similarity	NPD4615	Phase 2
0.6848	Remote Similarity	NPD2061	Approved
0.6845	Remote Similarity	NPD4912	Phase 3
0.6845	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3385	Approved
0.6839	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2096	Phase 2
0.6837	Remote Similarity	NPD2091	Phase 2
0.6832	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5017	Discontinued
0.6825	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7455	Approved
0.6825	Remote Similarity	NPD7454	Approved
0.6823	Remote Similarity	NPD5065	Approved
0.6823	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD201	Phase 2
0.6818	Remote Similarity	NPD200	Phase 2
0.6814	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5854	Approved
0.6814	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6999	Discontinued
0.6812	Remote Similarity	NPD5426	Phase 3
0.6812	Remote Similarity	NPD6987	Phase 1

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