NPASS Compound

Structure

NPC470209 OpenBabel07101719252D 29 33 0 0 1 0 0 0 0 0999 V2000 4.2007 2.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6254 -1.5682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 -3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 2.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9327 1.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 0.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2007 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2007 1.7728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 1.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 -0.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3347 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -4.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 1.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 0.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 7 16 1 0 0 0 0 7 17 2 0 0 0 0 8 15 1 0 0 0 0 8 27 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 2 1 6 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 5 1 1 0 0 0 13 27 1 0 0 0 0 14 6 1 1 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 25 2 0 0 0 0 17 20 1 0 0 0 0 17 29 1 0 0 0 0 19 20 1 0 0 0 0 20 24 2 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.18
Volume:	406.374
LogP:	6.242
LogD:	3.545
LogS:	-5.123
# Rotatable Bonds:	0
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	4.712
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.839
MDCK Permeability:	1.4441701750911307e-05
Pgp-inhibitor:	0.193
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	94.12972259521484%
Volume Distribution (VD):	0.668
Pgp-substrate:	5.548491954803467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.398
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.712
CYP2C9-substrate:	0.51
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	2.651
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.225
Carcinogencity:	0.668
Eye Corrosion:	0.003
Eye Irritation:	0.38
Respiratory Toxicity:	0.544

Download Data

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

Natural Product: NPC470209

Natural Product ID:	NPC470209
*Common Name:**	Oxodicitrinol A
IUPAC Name:	n.a.
Synonyms:	Oxodicitrinol A
Standard InCHIKey:	IMRZYAHXIQTVBH-DMTCVQMQSA-N
Standard InCHI:	InChI=1S/C24H26O5/c1-9-13(5)27-8-15-18(9)12(4)22(26)21-23(15)29-17-7-16(25)11(3)19-10(2)14(6)28-24(21)20(17)19/h7,9-10,13-14,26H,8H2,1-6H3/t9-,10-,13-,14-/m1/s1
SMILES:	C[C@H]1OCc2c([C@@H]1C)c(C)c(c1c2oc2cc(=O)c(c3c2c1O[C@@H]([C@H]3C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822983
PubChem CID:	53466207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8910.0	nM	PMID[573856]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[573856]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[573856]

☑ 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 NPC470209 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	415
0.1-0.2	1719
0.2-0.3	4013
0.3-0.4	9954
0.4-0.5	8788
0.5-0.6	3858
0.6-0.7	5573
0.7-0.8	5326
0.8-0.85	2337
0.85-0.9	675
0.9-0.95	38
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9085	High Similarity	NPC261502
0.9021	High Similarity	NPC10010
0.8561	High Similarity	NPC473107
0.8542	High Similarity	NPC36732
0.8489	Intermediate Similarity	NPC142563
0.8489	Intermediate Similarity	NPC1220
0.8489	Intermediate Similarity	NPC141822
0.8489	Intermediate Similarity	NPC291551
0.8489	Intermediate Similarity	NPC241165
0.8489	Intermediate Similarity	NPC177712
0.8489	Intermediate Similarity	NPC469965
0.8489	Intermediate Similarity	NPC205797
0.8489	Intermediate Similarity	NPC24913
0.8483	Intermediate Similarity	NPC101255
0.8483	Intermediate Similarity	NPC43716
0.8483	Intermediate Similarity	NPC475719
0.8444	Intermediate Similarity	NPC293801
0.8425	Intermediate Similarity	NPC471608
0.84	Intermediate Similarity	NPC87708
0.8358	Intermediate Similarity	NPC57199
0.8357	Intermediate Similarity	NPC77196
0.8355	Intermediate Similarity	NPC164244
0.8333	Intermediate Similarity	NPC472796
0.8333	Intermediate Similarity	NPC232645
0.8333	Intermediate Similarity	NPC472795
0.8333	Intermediate Similarity	NPC72958
0.8322	Intermediate Similarity	NPC278600
0.8322	Intermediate Similarity	NPC47040
0.8322	Intermediate Similarity	NPC144512
0.8322	Intermediate Similarity	NPC137262
0.8322	Intermediate Similarity	NPC37428
0.8322	Intermediate Similarity	NPC35501
0.8321	Intermediate Similarity	NPC473134
0.8312	Intermediate Similarity	NPC472618
0.8311	Intermediate Similarity	NPC142863
0.8309	Intermediate Similarity	NPC476653
0.8298	Intermediate Similarity	NPC184677
0.8286	Intermediate Similarity	NPC472798
0.8278	Intermediate Similarity	NPC223720
0.8276	Intermediate Similarity	NPC93640
0.8276	Intermediate Similarity	NPC20631
0.8261	Intermediate Similarity	NPC60704
0.8261	Intermediate Similarity	NPC139595
0.8261	Intermediate Similarity	NPC38604
0.8261	Intermediate Similarity	NPC293642
0.8261	Intermediate Similarity	NPC211179
0.8252	Intermediate Similarity	NPC309452
0.8247	Intermediate Similarity	NPC472617
0.8247	Intermediate Similarity	NPC186113
0.8227	Intermediate Similarity	NPC83535
0.8227	Intermediate Similarity	NPC185777
0.8224	Intermediate Similarity	NPC472799
0.8224	Intermediate Similarity	NPC268484
0.8224	Intermediate Similarity	NPC60084
0.8214	Intermediate Similarity	NPC118683
0.8214	Intermediate Similarity	NPC66430
0.8214	Intermediate Similarity	NPC293203
0.8214	Intermediate Similarity	NPC68205
0.8214	Intermediate Similarity	NPC244888
0.8214	Intermediate Similarity	NPC211413
0.8214	Intermediate Similarity	NPC37009
0.8214	Intermediate Similarity	NPC164804
0.8214	Intermediate Similarity	NPC160623
0.8207	Intermediate Similarity	NPC265075
0.8207	Intermediate Similarity	NPC472523
0.8205	Intermediate Similarity	NPC473022
0.8205	Intermediate Similarity	NPC15374
0.8201	Intermediate Similarity	NPC472797
0.82	Intermediate Similarity	NPC288036
0.82	Intermediate Similarity	NPC97029
0.82	Intermediate Similarity	NPC100985
0.82	Intermediate Similarity	NPC97028
0.82	Intermediate Similarity	NPC65589
0.82	Intermediate Similarity	NPC158338
0.8182	Intermediate Similarity	NPC472800
0.8182	Intermediate Similarity	NPC158542
0.8182	Intermediate Similarity	NPC272196
0.8176	Intermediate Similarity	NPC233980
0.817	Intermediate Similarity	NPC267242
0.8169	Intermediate Similarity	NPC225696
0.8169	Intermediate Similarity	NPC97834
0.8169	Intermediate Similarity	NPC223008
0.8169	Intermediate Similarity	NPC198154
0.8169	Intermediate Similarity	NPC115335
0.8169	Intermediate Similarity	NPC296915
0.8165	Intermediate Similarity	NPC272502
0.8162	Intermediate Similarity	NPC96940
0.8151	Intermediate Similarity	NPC469818
0.8146	Intermediate Similarity	NPC150928
0.8143	Intermediate Similarity	NPC27187
0.8143	Intermediate Similarity	NPC470225
0.8141	Intermediate Similarity	NPC18380
0.8134	Intermediate Similarity	NPC282255
0.8134	Intermediate Similarity	NPC3239
0.8133	Intermediate Similarity	NPC27221
0.8133	Intermediate Similarity	NPC256672
0.8133	Intermediate Similarity	NPC470208
0.8133	Intermediate Similarity	NPC295573
0.8133	Intermediate Similarity	NPC7025
0.8129	Intermediate Similarity	NPC38664
0.8129	Intermediate Similarity	NPC4950
0.8129	Intermediate Similarity	NPC195167
0.8129	Intermediate Similarity	NPC239118
0.8129	Intermediate Similarity	NPC53986
0.8121	Intermediate Similarity	NPC470676
0.8121	Intermediate Similarity	NPC473135
0.8121	Intermediate Similarity	NPC473132
0.8113	Intermediate Similarity	NPC45760
0.8108	Intermediate Similarity	NPC469557
0.8108	Intermediate Similarity	NPC86069
0.8105	Intermediate Similarity	NPC188578
0.8105	Intermediate Similarity	NPC135522
0.8105	Intermediate Similarity	NPC329844
0.8105	Intermediate Similarity	NPC169990
0.8105	Intermediate Similarity	NPC210942
0.8105	Intermediate Similarity	NPC80918
0.8101	Intermediate Similarity	NPC469664
0.8099	Intermediate Similarity	NPC469955
0.8099	Intermediate Similarity	NPC469952
0.8099	Intermediate Similarity	NPC469610
0.8092	Intermediate Similarity	NPC476452
0.8092	Intermediate Similarity	NPC478148
0.8092	Intermediate Similarity	NPC149526
0.8092	Intermediate Similarity	NPC474417
0.8089	Intermediate Similarity	NPC473961
0.8085	Intermediate Similarity	NPC164574
0.8085	Intermediate Similarity	NPC268917
0.8085	Intermediate Similarity	NPC280653
0.8085	Intermediate Similarity	NPC17343
0.8085	Intermediate Similarity	NPC12875
0.8085	Intermediate Similarity	NPC228369
0.8085	Intermediate Similarity	NPC129784
0.8085	Intermediate Similarity	NPC476166
0.8085	Intermediate Similarity	NPC300875
0.8085	Intermediate Similarity	NPC207892
0.8085	Intermediate Similarity	NPC118114
0.8085	Intermediate Similarity	NPC196765
0.8085	Intermediate Similarity	NPC206224
0.8085	Intermediate Similarity	NPC129106
0.8085	Intermediate Similarity	NPC181497
0.8085	Intermediate Similarity	NPC150011
0.8085	Intermediate Similarity	NPC271945
0.8085	Intermediate Similarity	NPC8899
0.8085	Intermediate Similarity	NPC236014
0.8082	Intermediate Similarity	NPC138149
0.8079	Intermediate Similarity	NPC241636
0.8079	Intermediate Similarity	NPC146014
0.8077	Intermediate Similarity	NPC292863
0.8077	Intermediate Similarity	NPC184326
0.8077	Intermediate Similarity	NPC186325
0.8071	Intermediate Similarity	NPC222108
0.8071	Intermediate Similarity	NPC16577
0.8071	Intermediate Similarity	NPC25729
0.8071	Intermediate Similarity	NPC96719
0.8071	Intermediate Similarity	NPC93962
0.8071	Intermediate Similarity	NPC474494
0.8071	Intermediate Similarity	NPC134360
0.8069	Intermediate Similarity	NPC32630
0.8067	Intermediate Similarity	NPC474108
0.8067	Intermediate Similarity	NPC22005
0.8067	Intermediate Similarity	NPC123202
0.8067	Intermediate Similarity	NPC7943
0.8067	Intermediate Similarity	NPC177995
0.8058	Intermediate Similarity	NPC149796
0.8056	Intermediate Similarity	NPC471522
0.8052	Intermediate Similarity	NPC55662
0.8052	Intermediate Similarity	NPC166054
0.805	Intermediate Similarity	NPC178173
0.8043	Intermediate Similarity	NPC232692
0.8043	Intermediate Similarity	NPC188022
0.8043	Intermediate Similarity	NPC102540
0.8043	Intermediate Similarity	NPC17809
0.8043	Intermediate Similarity	NPC285040
0.8043	Intermediate Similarity	NPC202594
0.8043	Intermediate Similarity	NPC105031
0.8043	Intermediate Similarity	NPC103420
0.8042	Intermediate Similarity	NPC131950
0.8041	Intermediate Similarity	NPC3732
0.8041	Intermediate Similarity	NPC473845
0.8041	Intermediate Similarity	NPC473108
0.8039	Intermediate Similarity	NPC40356
0.8039	Intermediate Similarity	NPC154683
0.8028	Intermediate Similarity	NPC165612
0.8028	Intermediate Similarity	NPC13005
0.8028	Intermediate Similarity	NPC469611
0.8026	Intermediate Similarity	NPC158866
0.8026	Intermediate Similarity	NPC202595
0.8026	Intermediate Similarity	NPC472633
0.8025	Intermediate Similarity	NPC137232
0.8025	Intermediate Similarity	NPC273467
0.8025	Intermediate Similarity	NPC189552
0.8013	Intermediate Similarity	NPC146388
0.8013	Intermediate Similarity	NPC85121
0.8013	Intermediate Similarity	NPC161191
0.8013	Intermediate Similarity	NPC177650
0.8	Intermediate Similarity	NPC476088
0.8	Intermediate Similarity	NPC24136
0.8	Intermediate Similarity	NPC470307
0.8	Intermediate Similarity	NPC474161
0.8	Intermediate Similarity	NPC469758

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 NPC470209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	1049
0.2-0.3	1812
0.3-0.4	2665
0.4-0.5	1801
0.5-0.6	942
0.6-0.7	346
0.7-0.8	133
0.8-0.85	26
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8489	Intermediate Similarity	NPD5124	Phase 1
0.8489	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD4749	Approved
0.8143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8071	Intermediate Similarity	NPD4625	Phase 3
0.8027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7877	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD6099	Approved
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD3750	Approved
0.7754	Intermediate Similarity	NPD1610	Phase 2
0.773	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2800	Approved
0.76	Intermediate Similarity	NPD6674	Discontinued
0.7582	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7340	Approved
0.7533	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD422	Phase 1
0.7483	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4626	Approved
0.7481	Intermediate Similarity	NPD1398	Phase 1
0.7468	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.745	Intermediate Similarity	NPD3748	Approved
0.7432	Intermediate Similarity	NPD6651	Approved
0.7431	Intermediate Similarity	NPD2861	Phase 2
0.7417	Intermediate Similarity	NPD1549	Phase 2
0.7415	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1613	Approved
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.741	Intermediate Similarity	NPD5691	Approved
0.7397	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1934	Approved
0.7343	Intermediate Similarity	NPD6696	Suspended
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7411	Suspended
0.7285	Intermediate Similarity	NPD2796	Approved
0.7284	Intermediate Similarity	NPD7075	Discontinued
0.726	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6166	Phase 2
0.7229	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5494	Approved
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7185	Intermediate Similarity	NPD4750	Phase 3
0.7179	Intermediate Similarity	NPD7213	Phase 3
0.7179	Intermediate Similarity	NPD7212	Phase 2
0.7178	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7985	Registered
0.7153	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD7644	Approved
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7124	Intermediate Similarity	NPD2346	Discontinued
0.7117	Intermediate Similarity	NPD4967	Phase 2
0.7117	Intermediate Similarity	NPD4965	Approved
0.7117	Intermediate Similarity	NPD4966	Approved
0.7108	Intermediate Similarity	NPD6232	Discontinued
0.7107	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD7054	Approved
0.7099	Intermediate Similarity	NPD2801	Approved
0.7097	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3027	Phase 3
0.7086	Intermediate Similarity	NPD1607	Approved
0.7081	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2424	Discontinued
0.707	Intermediate Similarity	NPD1511	Approved
0.707	Intermediate Similarity	NPD7390	Discontinued
0.7067	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD7472	Approved
0.7055	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD3268	Approved
0.7032	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6797	Phase 2
0.7013	Intermediate Similarity	NPD5762	Approved
0.7013	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD1465	Phase 2
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6993	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7003	Approved
0.6986	Remote Similarity	NPD3225	Approved
0.6986	Remote Similarity	NPD8651	Approved
0.6981	Remote Similarity	NPD1512	Approved
0.6977	Remote Similarity	NPD7251	Discontinued
0.6974	Remote Similarity	NPD4097	Suspended
0.697	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD3226	Approved
0.6954	Remote Similarity	NPD1240	Approved
0.6951	Remote Similarity	NPD5402	Approved
0.6948	Remote Similarity	NPD1551	Phase 2
0.6941	Remote Similarity	NPD3751	Discontinued
0.6937	Remote Similarity	NPD5403	Approved
0.6936	Remote Similarity	NPD7808	Phase 3
0.6923	Remote Similarity	NPD1651	Approved
0.6919	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5327	Phase 3
0.6914	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD3882	Suspended
0.6908	Remote Similarity	NPD5735	Approved
0.6903	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6004	Phase 3
0.6903	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD6002	Phase 3
0.6879	Remote Similarity	NPD3892	Phase 2
0.6879	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD6671	Approved
0.6875	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD1778	Approved
0.6871	Remote Similarity	NPD1283	Approved
0.6855	Remote Similarity	NPD7041	Phase 2
0.6855	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3817	Phase 2
0.6848	Remote Similarity	NPD4288	Approved
0.6845	Remote Similarity	NPD7199	Phase 2
0.6842	Remote Similarity	NPD3818	Discontinued
0.6839	Remote Similarity	NPD2935	Discontinued
0.6839	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7549	Discontinued
0.6828	Remote Similarity	NPD3496	Discontinued
0.6818	Remote Similarity	NPD7097	Phase 1
0.6816	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5401	Approved
0.6805	Remote Similarity	NPD3787	Discontinued
0.68	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7240	Approved
0.6781	Remote Similarity	NPD1611	Approved
0.6774	Remote Similarity	NPD7033	Discontinued
0.6774	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6353	Approved
0.675	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7458	Discontinued
0.6743	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4360	Phase 2
0.674	Remote Similarity	NPD4363	Phase 3
0.6732	Remote Similarity	NPD2979	Phase 3
0.6732	Remote Similarity	NPD3620	Phase 2
0.6732	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5405	Approved
0.6731	Remote Similarity	NPD2438	Suspended
0.6731	Remote Similarity	NPD5406	Approved
0.6731	Remote Similarity	NPD5408	Approved
0.6731	Remote Similarity	NPD5404	Approved
0.6728	Remote Similarity	NPD920	Approved
0.6726	Remote Similarity	NPD5709	Phase 3
0.6711	Remote Similarity	NPD1296	Phase 2
0.6711	Remote Similarity	NPD3266	Approved
0.6711	Remote Similarity	NPD3267	Approved
0.6709	Remote Similarity	NPD1243	Approved
0.6704	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD5929	Approved
0.6687	Remote Similarity	NPD8455	Phase 2
0.6687	Remote Similarity	NPD6667	Approved
0.6687	Remote Similarity	NPD6666	Approved
0.6686	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7466	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD1091	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6647	Remote Similarity	NPD8127	Discontinued
0.6647	Remote Similarity	NPD7177	Discontinued
0.6646	Remote Similarity	NPD7037	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