NPASS Compound

Structure

NPC475876 OpenBabel07101719142D 34 39 0 0 1 0 0 0 0 0999 V2000 -2.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.8660 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 -1.7321 -3.0000 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 0.0000 -4.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 0.8660 -3.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 28 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 17 27 1 6 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 29 1 1 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 31 1 6 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 29 1 1 0 0 0 23 34 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 30 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	6.002
LogD:	4.35
LogS:	-4.766
# Rotatable Bonds:	1
TPSA:	70.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	5.224
Fsp3:	0.9
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:	-5.415
MDCK Permeability:	1.4883045878377743e-05
Pgp-inhibitor:	0.493
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.501
Plasma Protein Binding (PPB):	90.3083724975586%
Volume Distribution (VD):	0.718
Pgp-substrate:	11.195647239685059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.309
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.29
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	4.095
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.603
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.778
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.056
Carcinogencity:	0.183
Eye Corrosion:	0.41
Eye Irritation:	0.133
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC475876

Natural Product ID:	NPC475876
*Common Name:**	DCSOSRBBKAIOTD-SCORLBCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCSOSRBBKAIOTD-SCORLBCFSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)14-15-30(24(32)33)13-9-18-28(6)11-8-17-26(3,4)20(31)10-12-27(17,5)22(28)21-23(34-21)29(18,7)19(30)16-25/h9,17,19-23,31H,8,10-16H2,1-7H3,(H,32,33)/t17-,19-,20-,21-,22+,23-,27-,28-,29+,30+/m0/s1
SMILES:	CC1(CCC2(CC=C3C4(CCC5C(C(CCC5(C4C6C(C3(C2C1)C)O6)C)O)(C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517792
PubChem CID:	11994580
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO14533	Gomphrena macrocephala	Species	Amaranthaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125230]
NPO14533	Gomphrena macrocephala	Species	Amaranthaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	=	21000.0	nM	PMID[450238]

☑ 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 NPC475876 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	239
0.1-0.2	1605
0.2-0.3	5042
0.3-0.4	11610
0.4-0.5	10707
0.5-0.6	5886
0.6-0.7	5149
0.7-0.8	2089
0.8-0.85	249
0.85-0.9	113
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC58942
0.9362	High Similarity	NPC260149
0.9247	High Similarity	NPC473240
0.9247	High Similarity	NPC474727
0.9149	High Similarity	NPC476318
0.9149	High Similarity	NPC476327
0.9053	High Similarity	NPC476879
0.9053	High Similarity	NPC476878
0.9053	High Similarity	NPC189880
0.9022	High Similarity	NPC474728
0.8936	High Similarity	NPC159365
0.8925	High Similarity	NPC77099
0.8925	High Similarity	NPC60755
0.8925	High Similarity	NPC470590
0.8925	High Similarity	NPC285184
0.8925	High Similarity	NPC475708
0.8913	High Similarity	NPC30522
0.8913	High Similarity	NPC198664
0.8913	High Similarity	NPC470588
0.8913	High Similarity	NPC143232
0.8913	High Similarity	NPC274330
0.883	High Similarity	NPC86368
0.8817	High Similarity	NPC470589
0.8817	High Similarity	NPC113989
0.8817	High Similarity	NPC111110
0.8817	High Similarity	NPC126369
0.8817	High Similarity	NPC120840
0.8804	High Similarity	NPC473242
0.8804	High Similarity	NPC52169
0.8804	High Similarity	NPC40552
0.8804	High Similarity	NPC474512
0.8804	High Similarity	NPC290690
0.8804	High Similarity	NPC181225
0.8804	High Similarity	NPC246708
0.8804	High Similarity	NPC182797
0.8804	High Similarity	NPC17733
0.8804	High Similarity	NPC470629
0.8791	High Similarity	NPC72638
0.875	High Similarity	NPC327179
0.8737	High Similarity	NPC474529
0.8723	High Similarity	NPC187722
0.871	High Similarity	NPC64872
0.871	High Similarity	NPC130520
0.871	High Similarity	NPC225585
0.871	High Similarity	NPC263393
0.871	High Similarity	NPC25906
0.871	High Similarity	NPC234346
0.871	High Similarity	NPC127689
0.871	High Similarity	NPC59263
0.871	High Similarity	NPC121798
0.871	High Similarity	NPC290972
0.871	High Similarity	NPC270768
0.871	High Similarity	NPC61543
0.871	High Similarity	NPC293048
0.8696	High Similarity	NPC98442
0.8696	High Similarity	NPC88716
0.8696	High Similarity	NPC171203
0.8696	High Similarity	NPC130577
0.8696	High Similarity	NPC142415
0.8696	High Similarity	NPC51700
0.8696	High Similarity	NPC242468
0.8696	High Similarity	NPC293564
0.8696	High Similarity	NPC102683
0.8696	High Similarity	NPC307426
0.8696	High Similarity	NPC68160
0.8696	High Similarity	NPC18064
0.866	High Similarity	NPC43686
0.8646	High Similarity	NPC139570
0.8646	High Similarity	NPC195715
0.8632	High Similarity	NPC136313
0.8632	High Similarity	NPC63118
0.8632	High Similarity	NPC118519
0.8632	High Similarity	NPC49776
0.8632	High Similarity	NPC229281
0.8632	High Similarity	NPC158059
0.8632	High Similarity	NPC202728
0.8632	High Similarity	NPC295643
0.8632	High Similarity	NPC307335
0.8632	High Similarity	NPC74855
0.8632	High Similarity	NPC214756
0.8632	High Similarity	NPC474436
0.8632	High Similarity	NPC272075
0.8617	High Similarity	NPC477872
0.8617	High Similarity	NPC18872
0.8617	High Similarity	NPC120968
0.8617	High Similarity	NPC227467
0.8617	High Similarity	NPC290614
0.8617	High Similarity	NPC130278
0.8617	High Similarity	NPC49320
0.8617	High Similarity	NPC210037
0.8617	High Similarity	NPC7260
0.8617	High Similarity	NPC273621
0.8617	High Similarity	NPC291028
0.8614	High Similarity	NPC278628
0.8614	High Similarity	NPC231530
0.86	High Similarity	NPC282233
0.86	High Similarity	NPC95585
0.8557	High Similarity	NPC230151
0.8557	High Similarity	NPC19376
0.8557	High Similarity	NPC305464
0.8557	High Similarity	NPC25848
0.8557	High Similarity	NPC307282
0.8544	High Similarity	NPC310546
0.8542	High Similarity	NPC474963
0.8542	High Similarity	NPC209868
0.8542	High Similarity	NPC184006
0.8542	High Similarity	NPC6818
0.8542	High Similarity	NPC191412
0.8542	High Similarity	NPC74751
0.8542	High Similarity	NPC91010
0.8542	High Similarity	NPC78580
0.8542	High Similarity	NPC23621
0.8542	High Similarity	NPC114159
0.8542	High Similarity	NPC296164
0.8526	High Similarity	NPC474525
0.8526	High Similarity	NPC52021
0.8526	High Similarity	NPC324341
0.8526	High Similarity	NPC158030
0.8526	High Similarity	NPC282616
0.8526	High Similarity	NPC288833
0.8526	High Similarity	NPC966
0.8526	High Similarity	NPC71074
0.8526	High Similarity	NPC300351
0.8526	High Similarity	NPC65120
0.8526	High Similarity	NPC84319
0.8526	High Similarity	NPC145067
0.8526	High Similarity	NPC472149
0.8526	High Similarity	NPC155120
0.8526	High Similarity	NPC25299
0.8526	High Similarity	NPC306541
0.8526	High Similarity	NPC233455
0.8526	High Similarity	NPC4036
0.8526	High Similarity	NPC38754
0.8526	High Similarity	NPC228784
0.8526	High Similarity	NPC105189
0.8526	High Similarity	NPC235884
0.8515	High Similarity	NPC475036
0.8511	High Similarity	NPC95246
0.8511	High Similarity	NPC474972
0.8511	High Similarity	NPC474686
0.8511	High Similarity	NPC161751
0.8495	Intermediate Similarity	NPC71507
0.8495	Intermediate Similarity	NPC162107
0.8495	Intermediate Similarity	NPC46912
0.8469	Intermediate Similarity	NPC259788
0.8469	Intermediate Similarity	NPC255589
0.8469	Intermediate Similarity	NPC158347
0.8454	Intermediate Similarity	NPC96916
0.8454	Intermediate Similarity	NPC198245
0.8454	Intermediate Similarity	NPC23241
0.8447	Intermediate Similarity	NPC275539
0.8447	Intermediate Similarity	NPC94529
0.8447	Intermediate Similarity	NPC189075
0.8438	Intermediate Similarity	NPC474806
0.8438	Intermediate Similarity	NPC133579
0.8438	Intermediate Similarity	NPC275809
0.8438	Intermediate Similarity	NPC298554
0.8431	Intermediate Similarity	NPC477877
0.8421	Intermediate Similarity	NPC86372
0.8421	Intermediate Similarity	NPC172361
0.8421	Intermediate Similarity	NPC46441
0.8421	Intermediate Similarity	NPC193750
0.8416	Intermediate Similarity	NPC95899
0.8416	Intermediate Similarity	NPC275583
0.84	Intermediate Similarity	NPC476132
0.84	Intermediate Similarity	NPC118964
0.84	Intermediate Similarity	NPC256247
0.84	Intermediate Similarity	NPC54909
0.84	Intermediate Similarity	NPC233012
0.8387	Intermediate Similarity	NPC56588
0.8387	Intermediate Similarity	NPC329943
0.8387	Intermediate Similarity	NPC73038
0.8387	Intermediate Similarity	NPC9892
0.8387	Intermediate Similarity	NPC10005
0.8387	Intermediate Similarity	NPC91525
0.8387	Intermediate Similarity	NPC325594
0.8384	Intermediate Similarity	NPC471966
0.8384	Intermediate Similarity	NPC164349
0.837	Intermediate Similarity	NPC171789
0.8367	Intermediate Similarity	NPC73004
0.8367	Intermediate Similarity	NPC116457
0.8367	Intermediate Similarity	NPC204961
0.8367	Intermediate Similarity	NPC173744
0.8367	Intermediate Similarity	NPC158371
0.8367	Intermediate Similarity	NPC259733
0.8367	Intermediate Similarity	NPC98874
0.8367	Intermediate Similarity	NPC157113
0.8367	Intermediate Similarity	NPC207922
0.8367	Intermediate Similarity	NPC62516
0.8367	Intermediate Similarity	NPC132824
0.8351	Intermediate Similarity	NPC188102
0.8351	Intermediate Similarity	NPC87095
0.8351	Intermediate Similarity	NPC32407
0.8351	Intermediate Similarity	NPC299996
0.8351	Intermediate Similarity	NPC282395
0.8351	Intermediate Similarity	NPC80365
0.8351	Intermediate Similarity	NPC20235
0.8351	Intermediate Similarity	NPC263548
0.8351	Intermediate Similarity	NPC88116
0.8351	Intermediate Similarity	NPC60692

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 NPC475876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1903
0.2-0.3	3837
0.3-0.4	2107
0.4-0.5	649
0.5-0.6	235
0.6-0.7	183
0.7-0.8	23
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD7748	Approved
0.8526	High Similarity	NPD7515	Phase 2
0.8283	Intermediate Similarity	NPD7902	Approved
0.798	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD7900	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.7838	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7736	Intermediate Similarity	NPD6008	Approved
0.7708	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6399	Phase 3
0.7634	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD6411	Approved
0.76	Intermediate Similarity	NPD8035	Phase 2
0.76	Intermediate Similarity	NPD8034	Phase 2
0.7586	Intermediate Similarity	NPD8328	Phase 3
0.7576	Intermediate Similarity	NPD5328	Approved
0.757	Intermediate Similarity	NPD7128	Approved
0.757	Intermediate Similarity	NPD6675	Approved
0.757	Intermediate Similarity	NPD5739	Approved
0.757	Intermediate Similarity	NPD6402	Approved
0.7523	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6881	Approved
0.7431	Intermediate Similarity	NPD6899	Approved
0.7431	Intermediate Similarity	NPD7320	Approved
0.7426	Intermediate Similarity	NPD6079	Approved
0.7423	Intermediate Similarity	NPD4786	Approved
0.74	Intermediate Similarity	NPD6101	Approved
0.74	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3667	Approved
0.7374	Intermediate Similarity	NPD3573	Approved
0.7364	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6373	Approved
0.7364	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5778	Approved
0.7353	Intermediate Similarity	NPD5779	Approved
0.7339	Intermediate Similarity	NPD5701	Approved
0.7339	Intermediate Similarity	NPD5697	Approved
0.73	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7290	Approved
0.7297	Intermediate Similarity	NPD7102	Approved
0.7297	Intermediate Similarity	NPD6883	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD6011	Approved
0.7257	Intermediate Similarity	NPD4632	Approved
0.7232	Intermediate Similarity	NPD6617	Approved
0.7232	Intermediate Similarity	NPD6869	Approved
0.7232	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6650	Approved
0.7232	Intermediate Similarity	NPD6847	Approved
0.7232	Intermediate Similarity	NPD6649	Approved
0.7232	Intermediate Similarity	NPD8130	Phase 1
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7207	Intermediate Similarity	NPD6013	Approved
0.7207	Intermediate Similarity	NPD6012	Approved
0.7207	Intermediate Similarity	NPD6014	Approved
0.7168	Intermediate Similarity	NPD8297	Approved
0.7168	Intermediate Similarity	NPD6882	Approved
0.7158	Intermediate Similarity	NPD6697	Approved
0.7158	Intermediate Similarity	NPD6118	Approved
0.7158	Intermediate Similarity	NPD6115	Approved
0.7158	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD4755	Approved
0.7075	Intermediate Similarity	NPD5173	Approved
0.7069	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7034	Intermediate Similarity	NPD6319	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7025	Intermediate Similarity	NPD7507	Approved
0.6983	Remote Similarity	NPD6868	Approved
0.6981	Remote Similarity	NPD7614	Phase 1
0.6975	Remote Similarity	NPD5983	Phase 2
0.6961	Remote Similarity	NPD5737	Approved
0.6961	Remote Similarity	NPD6672	Approved
0.6961	Remote Similarity	NPD6903	Approved
0.6947	Remote Similarity	NPD6117	Approved
0.6944	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD4696	Approved
0.6944	Remote Similarity	NPD5285	Approved
0.6944	Remote Similarity	NPD5286	Approved
0.6942	Remote Similarity	NPD7492	Approved
0.69	Remote Similarity	NPD3666	Approved
0.69	Remote Similarity	NPD3665	Phase 1
0.69	Remote Similarity	NPD3133	Approved
0.69	Remote Similarity	NPD3668	Phase 3
0.6891	Remote Similarity	NPD6059	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6336	Discontinued
0.6885	Remote Similarity	NPD6616	Approved
0.6881	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6116	Phase 1
0.6864	Remote Similarity	NPD6335	Approved
0.6857	Remote Similarity	NPD4202	Approved
0.6855	Remote Similarity	NPD7319	Approved
0.6842	Remote Similarity	NPD3703	Phase 2
0.6838	Remote Similarity	NPD6274	Approved
0.6837	Remote Similarity	NPD7525	Registered
0.6829	Remote Similarity	NPD8293	Discontinued
0.6829	Remote Similarity	NPD7078	Approved
0.6822	Remote Similarity	NPD7732	Phase 3
0.6818	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD5224	Approved
0.6818	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD4633	Approved
0.6814	Remote Similarity	NPD6686	Approved
0.681	Remote Similarity	NPD8133	Approved
0.6807	Remote Similarity	NPD7101	Approved
0.6807	Remote Similarity	NPD7100	Approved
0.678	Remote Similarity	NPD6317	Approved
0.6777	Remote Similarity	NPD6370	Approved
0.6757	Remote Similarity	NPD4754	Approved
0.6757	Remote Similarity	NPD5174	Approved
0.6757	Remote Similarity	NPD5175	Approved
0.6737	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5695	Phase 3
0.6724	Remote Similarity	NPD6053	Discontinued
0.6723	Remote Similarity	NPD6313	Approved
0.6723	Remote Similarity	NPD6314	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6697	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD6909	Approved
0.6694	Remote Similarity	NPD6908	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6637	Remote Similarity	NPD4767	Approved
0.6637	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6098	Approved
0.6598	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6673	Approved
0.6571	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD4753	Phase 2
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8033	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8516	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4730	Approved
0.6522	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD5168	Approved
0.6522	Remote Similarity	NPD4729	Approved
0.6508	Remote Similarity	NPD6033	Approved
0.6505	Remote Similarity	NPD1694	Approved
0.6481	Remote Similarity	NPD6001	Approved
0.6475	Remote Similarity	NPD8294	Approved
0.6475	Remote Similarity	NPD8377	Approved
0.6452	Remote Similarity	NPD6067	Discontinued
0.6449	Remote Similarity	NPD7983	Approved
0.6446	Remote Similarity	NPD7327	Approved
0.6446	Remote Similarity	NPD7328	Approved
0.6442	Remote Similarity	NPD6422	Discontinued
0.6442	Remote Similarity	NPD5279	Phase 3
0.6429	Remote Similarity	NPD5344	Discontinued
0.6423	Remote Similarity	NPD6921	Approved
0.6423	Remote Similarity	NPD8380	Approved
0.6423	Remote Similarity	NPD8335	Approved
0.6423	Remote Similarity	NPD8378	Approved
0.6423	Remote Similarity	NPD8379	Approved
0.6423	Remote Similarity	NPD8296	Approved
0.641	Remote Similarity	NPD5247	Approved
0.641	Remote Similarity	NPD5135	Approved
0.641	Remote Similarity	NPD5249	Phase 3
0.641	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5248	Approved
0.641	Remote Similarity	NPD5250	Approved
0.641	Remote Similarity	NPD5251	Approved
0.641	Remote Similarity	NPD5169	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