NPASS Compound

Structure

NPC470721 OpenBabel07101719152D 21 22 0 0 1 0 0 0 0 0999 V2000 0.4288 -1.6003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5242 -0.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4783 2.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6764 -0.6764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8284 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8284 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6567 1.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 2.7414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8837 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 1.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 5 21 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 4 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.13
Volume:	298.948
LogP:	1.936
LogD:	1.842
LogS:	-3.822
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	3.629
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.649
MDCK Permeability:	1.2409377632138785e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	55.484092712402344%
Volume Distribution (VD):	1.488
Pgp-substrate:	35.051570892333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.847

ADMET: Excretion

Clearance (CL):	2.012
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.398
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.054
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC470721

Natural Product ID:	NPC470721
*Common Name:**	(1S,4S)-1,4-Dihydroxy-7-Methoxy-1,6-Dimethyl-4-Propan-2-Ylnaphthalene-2,3-Dione
IUPAC Name:	(1S,4S)-1,4-dihydroxy-7-methoxy-1,6-dimethyl-4-propan-2-ylnaphthalene-2,3-dione
Synonyms:
Standard InCHIKey:	SSMLCQMNNLXFLS-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C16H20O5/c1-8(2)16(20)11-6-9(3)12(21-5)7-10(11)15(4,19)13(17)14(16)18/h6-8,19-20H,1-5H3/t15-,16-/m0/s1
SMILES:	COc1cc2c(cc1C)[C@@](O)(C(C)C)C(=O)C(=O)[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206795
PubChem CID:	71461416
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32770	sterculia tavia	Species	Malvaceae	Eukaryota	n.a.	Madagascar Rain Forest	n.a.	PMID[23149304]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5900.0	nM	PMID[497652]

☑ 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 NPC470721 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	354
0.1-0.2	1516
0.2-0.3	3331
0.3-0.4	8491
0.4-0.5	10455
0.5-0.6	3899
0.6-0.7	8205
0.7-0.8	6157
0.8-0.85	263
0.85-0.9	20
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470722
1.0	High Similarity	NPC6100
1.0	High Similarity	NPC156888
0.9462	High Similarity	NPC470725
0.9173	High Similarity	NPC312560
0.8913	High Similarity	NPC475104
0.8794	High Similarity	NPC201297
0.8759	High Similarity	NPC213122
0.8741	High Similarity	NPC253488
0.8705	High Similarity	NPC98804
0.8633	High Similarity	NPC471670
0.8633	High Similarity	NPC475549
0.863	High Similarity	NPC329933
0.8621	High Similarity	NPC34802
0.8601	High Similarity	NPC84266
0.8571	High Similarity	NPC290601
0.8561	High Similarity	NPC22644
0.8533	High Similarity	NPC474360
0.8531	High Similarity	NPC182255
0.8531	High Similarity	NPC94076
0.8529	High Similarity	NPC206028
0.8446	Intermediate Similarity	NPC294646
0.8444	Intermediate Similarity	NPC474737
0.8425	Intermediate Similarity	NPC163846
0.8425	Intermediate Similarity	NPC225173
0.8414	Intermediate Similarity	NPC471305
0.8414	Intermediate Similarity	NPC477409
0.8414	Intermediate Similarity	NPC471451
0.8392	Intermediate Similarity	NPC136649
0.8392	Intermediate Similarity	NPC168471
0.8389	Intermediate Similarity	NPC149526
0.8389	Intermediate Similarity	NPC474417
0.8389	Intermediate Similarity	NPC478148
0.8378	Intermediate Similarity	NPC97028
0.8378	Intermediate Similarity	NPC158338
0.8378	Intermediate Similarity	NPC97029
0.8378	Intermediate Similarity	NPC100985
0.8378	Intermediate Similarity	NPC288036
0.8378	Intermediate Similarity	NPC65589
0.8367	Intermediate Similarity	NPC312929
0.8367	Intermediate Similarity	NPC289042
0.8367	Intermediate Similarity	NPC245584
0.8367	Intermediate Similarity	NPC56433
0.8367	Intermediate Similarity	NPC125801
0.8367	Intermediate Similarity	NPC126767
0.8367	Intermediate Similarity	NPC190648
0.8367	Intermediate Similarity	NPC118027
0.8366	Intermediate Similarity	NPC284495
0.8358	Intermediate Similarity	NPC273683
0.8356	Intermediate Similarity	NPC328623
0.8356	Intermediate Similarity	NPC28632
0.8344	Intermediate Similarity	NPC68727
0.8333	Intermediate Similarity	NPC51824
0.8333	Intermediate Similarity	NPC470337
0.8333	Intermediate Similarity	NPC87708
0.8333	Intermediate Similarity	NPC470340
0.8333	Intermediate Similarity	NPC113608
0.8333	Intermediate Similarity	NPC470338
0.8333	Intermediate Similarity	NPC124365
0.8333	Intermediate Similarity	NPC470727
0.8333	Intermediate Similarity	NPC268992
0.8333	Intermediate Similarity	NPC180944
0.8322	Intermediate Similarity	NPC147735
0.8322	Intermediate Similarity	NPC158866
0.8322	Intermediate Similarity	NPC470568
0.8322	Intermediate Similarity	NPC1268
0.8312	Intermediate Similarity	NPC219686
0.8311	Intermediate Similarity	NPC472841
0.8311	Intermediate Similarity	NPC2569
0.8311	Intermediate Similarity	NPC256672
0.8311	Intermediate Similarity	NPC27221
0.8311	Intermediate Similarity	NPC7025
0.8311	Intermediate Similarity	NPC172329
0.8309	Intermediate Similarity	NPC470724
0.8299	Intermediate Similarity	NPC58752
0.8296	Intermediate Similarity	NPC75432
0.8288	Intermediate Similarity	NPC260152
0.8288	Intermediate Similarity	NPC169942
0.8278	Intermediate Similarity	NPC169990
0.8278	Intermediate Similarity	NPC210942
0.8278	Intermediate Similarity	NPC329844
0.8276	Intermediate Similarity	NPC126534
0.8276	Intermediate Similarity	NPC40118
0.8276	Intermediate Similarity	NPC49108
0.8276	Intermediate Similarity	NPC232021
0.8273	Intermediate Similarity	NPC239134
0.8273	Intermediate Similarity	NPC164295
0.8267	Intermediate Similarity	NPC470569
0.8267	Intermediate Similarity	NPC72958
0.8267	Intermediate Similarity	NPC232645
0.8267	Intermediate Similarity	NPC75377
0.8264	Intermediate Similarity	NPC109232
0.8264	Intermediate Similarity	NPC472366
0.8264	Intermediate Similarity	NPC165172
0.8255	Intermediate Similarity	NPC269420
0.8255	Intermediate Similarity	NPC233267
0.8255	Intermediate Similarity	NPC80370
0.8255	Intermediate Similarity	NPC291049
0.8243	Intermediate Similarity	NPC123202
0.8243	Intermediate Similarity	NPC7943
0.8243	Intermediate Similarity	NPC470757
0.8243	Intermediate Similarity	NPC22005
0.8243	Intermediate Similarity	NPC478018
0.8243	Intermediate Similarity	NPC259632
0.8235	Intermediate Similarity	NPC474637
0.8235	Intermediate Similarity	NPC470726
0.8235	Intermediate Similarity	NPC272196
0.8235	Intermediate Similarity	NPC477213
0.8231	Intermediate Similarity	NPC478019
0.8227	Intermediate Similarity	NPC27394
0.8224	Intermediate Similarity	NPC471456
0.8219	Intermediate Similarity	NPC3732
0.8219	Intermediate Similarity	NPC167663
0.8219	Intermediate Similarity	NPC53016
0.8219	Intermediate Similarity	NPC297600
0.8214	Intermediate Similarity	NPC165612
0.8214	Intermediate Similarity	NPC183103
0.8212	Intermediate Similarity	NPC273483
0.8212	Intermediate Similarity	NPC40356
0.8212	Intermediate Similarity	NPC154683
0.8212	Intermediate Similarity	NPC142527
0.8212	Intermediate Similarity	NPC45934
0.8212	Intermediate Similarity	NPC175978
0.8212	Intermediate Similarity	NPC217447
0.8207	Intermediate Similarity	NPC265178
0.82	Intermediate Similarity	NPC227122
0.82	Intermediate Similarity	NPC255641
0.82	Intermediate Similarity	NPC150928
0.82	Intermediate Similarity	NPC225854
0.82	Intermediate Similarity	NPC202595
0.82	Intermediate Similarity	NPC290954
0.8194	Intermediate Similarity	NPC21350
0.8194	Intermediate Similarity	NPC477408
0.8194	Intermediate Similarity	NPC470407
0.8194	Intermediate Similarity	NPC472368
0.8188	Intermediate Similarity	NPC37139
0.8188	Intermediate Similarity	NPC181675
0.8188	Intermediate Similarity	NPC105415
0.8182	Intermediate Similarity	NPC228654
0.8182	Intermediate Similarity	NPC24394
0.8176	Intermediate Similarity	NPC473135
0.8176	Intermediate Similarity	NPC300540
0.8176	Intermediate Similarity	NPC473132
0.8176	Intermediate Similarity	NPC470676
0.8176	Intermediate Similarity	NPC124729
0.817	Intermediate Similarity	NPC4547
0.817	Intermediate Similarity	NPC180924
0.8169	Intermediate Similarity	NPC281513
0.8169	Intermediate Similarity	NPC152209
0.8169	Intermediate Similarity	NPC22222
0.8165	Intermediate Similarity	NPC473094
0.8163	Intermediate Similarity	NPC245482
0.8163	Intermediate Similarity	NPC301751
0.8163	Intermediate Similarity	NPC189650
0.8163	Intermediate Similarity	NPC19896
0.8162	Intermediate Similarity	NPC111088
0.8158	Intermediate Similarity	NPC280530
0.8158	Intermediate Similarity	NPC178964
0.8158	Intermediate Similarity	NPC93552
0.8158	Intermediate Similarity	NPC193200
0.8158	Intermediate Similarity	NPC95842
0.8158	Intermediate Similarity	NPC477691
0.8158	Intermediate Similarity	NPC135522
0.8158	Intermediate Similarity	NPC472799
0.8156	Intermediate Similarity	NPC59459
0.8153	Intermediate Similarity	NPC316262
0.8153	Intermediate Similarity	NPC314653
0.8151	Intermediate Similarity	NPC11314
0.8151	Intermediate Similarity	NPC308572
0.8151	Intermediate Similarity	NPC250755
0.8146	Intermediate Similarity	NPC470675
0.8146	Intermediate Similarity	NPC473131
0.8146	Intermediate Similarity	NPC133856
0.8146	Intermediate Similarity	NPC302783
0.8146	Intermediate Similarity	NPC230848
0.8146	Intermediate Similarity	NPC473201
0.8143	Intermediate Similarity	NPC205360
0.8143	Intermediate Similarity	NPC474143
0.8143	Intermediate Similarity	NPC474246
0.8143	Intermediate Similarity	NPC258073
0.8138	Intermediate Similarity	NPC477956
0.8134	Intermediate Similarity	NPC129176
0.8133	Intermediate Similarity	NPC65775
0.8133	Intermediate Similarity	NPC10027
0.8129	Intermediate Similarity	NPC470810
0.8129	Intermediate Similarity	NPC313368
0.8125	Intermediate Similarity	NPC475028
0.8125	Intermediate Similarity	NPC317119
0.8125	Intermediate Similarity	NPC153979
0.8125	Intermediate Similarity	NPC476025
0.8117	Intermediate Similarity	NPC212967
0.8117	Intermediate Similarity	NPC282390
0.8117	Intermediate Similarity	NPC201127
0.8117	Intermediate Similarity	NPC246647
0.8117	Intermediate Similarity	NPC44199
0.8117	Intermediate Similarity	NPC96342
0.8117	Intermediate Similarity	NPC164110
0.8117	Intermediate Similarity	NPC281137
0.8117	Intermediate Similarity	NPC263483
0.8116	Intermediate Similarity	NPC477212

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 NPC470721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	982
0.2-0.3	1579
0.3-0.4	2605
0.4-0.5	1908
0.5-0.6	1102
0.6-0.7	530
0.7-0.8	123
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
0.8162	Intermediate Similarity	NPD1283	Approved
0.812	Intermediate Similarity	NPD1651	Approved
0.8108	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6100	Approved
0.8056	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7945	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1281	Approved
0.7931	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD3226	Approved
0.7875	Intermediate Similarity	NPD7473	Discontinued
0.7848	Intermediate Similarity	NPD6959	Discontinued
0.7847	Intermediate Similarity	NPD1607	Approved
0.7832	Intermediate Similarity	NPD2979	Phase 3
0.7806	Intermediate Similarity	NPD7819	Suspended
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7794	Intermediate Similarity	NPD4626	Approved
0.7755	Intermediate Similarity	NPD2346	Discontinued
0.7754	Intermediate Similarity	NPD1608	Approved
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7708	Intermediate Similarity	NPD1240	Approved
0.7698	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6696	Suspended
0.7619	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7619	Intermediate Similarity	NPD1510	Phase 2
0.76	Intermediate Similarity	NPD7003	Approved
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7536	Intermediate Similarity	NPD17	Approved
0.7532	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD1512	Approved
0.7468	Intermediate Similarity	NPD2801	Approved
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5691	Approved
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.745	Intermediate Similarity	NPD2438	Suspended
0.745	Intermediate Similarity	NPD2531	Phase 2
0.7448	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7075	Discontinued
0.7436	Intermediate Similarity	NPD7458	Discontinued
0.7429	Intermediate Similarity	NPD1201	Approved
0.7417	Intermediate Similarity	NPD2800	Approved
0.7415	Intermediate Similarity	NPD6355	Discontinued
0.7413	Intermediate Similarity	NPD2798	Approved
0.7413	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2932	Approved
0.741	Intermediate Similarity	NPD3019	Approved
0.7405	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD37	Approved
0.74	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3300	Phase 2
0.7383	Intermediate Similarity	NPD7033	Discontinued
0.7375	Intermediate Similarity	NPD3882	Suspended
0.7372	Intermediate Similarity	NPD7340	Approved
0.7362	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD5710	Approved
0.7362	Intermediate Similarity	NPD3787	Discontinued
0.7361	Intermediate Similarity	NPD2861	Phase 2
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD1470	Approved
0.7342	Intermediate Similarity	NPD7411	Suspended
0.7338	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD4476	Approved
0.7333	Intermediate Similarity	NPD4477	Approved
0.7324	Intermediate Similarity	NPD4749	Approved
0.7312	Intermediate Similarity	NPD3817	Phase 2
0.7305	Intermediate Similarity	NPD1611	Approved
0.7303	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.729	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD2344	Approved
0.7285	Intermediate Similarity	NPD5762	Approved
0.7279	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD1398	Phase 1
0.7273	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD3750	Approved
0.7251	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4097	Suspended
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD5404	Approved
0.7219	Intermediate Similarity	NPD5405	Approved
0.7219	Intermediate Similarity	NPD5406	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2313	Discontinued
0.7211	Intermediate Similarity	NPD3268	Approved
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8150	Discontinued
0.7206	Intermediate Similarity	NPD7635	Approved
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7178	Intermediate Similarity	NPD6234	Discontinued
0.7174	Intermediate Similarity	NPD6671	Approved
0.7172	Intermediate Similarity	NPD4624	Approved
0.7171	Intermediate Similarity	NPD6005	Phase 3
0.7171	Intermediate Similarity	NPD6004	Phase 3
0.7171	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6002	Phase 3
0.7151	Intermediate Similarity	NPD6776	Approved
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2230	Approved
0.7133	Intermediate Similarity	NPD2232	Approved
0.7133	Intermediate Similarity	NPD2233	Approved
0.7117	Intermediate Similarity	NPD3749	Approved
0.7113	Intermediate Similarity	NPD3023	Approved
0.7113	Intermediate Similarity	NPD3026	Approved
0.711	Intermediate Similarity	NPD8434	Phase 2
0.7108	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD2309	Approved
0.7095	Intermediate Similarity	NPD7985	Registered
0.7095	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD3024	Approved
0.7092	Intermediate Similarity	NPD3025	Approved
0.7083	Intermediate Similarity	NPD7177	Discontinued
0.7075	Intermediate Similarity	NPD4908	Phase 1
0.7071	Intermediate Similarity	NPD7644	Approved
0.7066	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7768	Phase 2
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7044	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7033	Intermediate Similarity	NPD7696	Phase 3
0.7033	Intermediate Similarity	NPD7435	Discontinued
0.7033	Intermediate Similarity	NPD7698	Approved
0.7033	Intermediate Similarity	NPD7697	Approved
0.7029	Intermediate Similarity	NPD5283	Phase 1
0.7025	Intermediate Similarity	NPD6273	Approved
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2238	Phase 2
0.7	Intermediate Similarity	NPD4140	Approved
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD5402	Approved
0.6993	Remote Similarity	NPD1551	Phase 2
0.6993	Remote Similarity	NPD3847	Discontinued
0.6988	Remote Similarity	NPD7199	Phase 2
0.6988	Remote Similarity	NPD1247	Approved
0.6972	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1243	Approved
0.6968	Remote Similarity	NPD6674	Discontinued
0.6966	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6797	Phase 2
0.6957	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1535	Discovery
0.6944	Remote Similarity	NPD1610	Phase 2
0.6933	Remote Similarity	NPD5760	Phase 2
0.6933	Remote Similarity	NPD6663	Approved
0.6933	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD4109	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