NPASS Compound

Structure

NPC472689 OpenBabel07101719132D 36 38 0 0 1 0 0 0 0 0999 V2000 2.9873 -3.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7626 -4.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2428 -4.2483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9056 -2.6481 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4263 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3143 -3.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1884 -2.8741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0579 -1.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0214 -3.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1123 -3.2568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 29 1 0 0 0 0 15 21 1 0 0 0 0 16 28 1 0 0 0 0 16 30 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 27 1 6 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 31 2 0 0 0 0 24 29 1 0 0 0 0 24 32 1 0 0 0 0 25 30 1 0 0 0 0 25 33 2 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 34 2 0 0 0 0 27 7 1 1 0 0 0 27 35 1 0 0 0 0 28 8 1 1 0 0 0 28 36 1 0 0 0 0 30 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	538.689
LogP:	4.491
LogD:	1.649
LogS:	-3.669
# Rotatable Bonds:	6
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	5.609
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	1.2932540812471416e-05
Pgp-inhibitor:	0.171
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	95.4457015991211%
Volume Distribution (VD):	1.765
Pgp-substrate:	6.325474262237549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.369
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	5.264
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.028
Carcinogencity:	0.471
Eye Corrosion:	0.836
Eye Irritation:	0.072
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC472689

Natural Product ID:	NPC472689
*Common Name:**	KQTPSADZOFBZMJ-QAYKPRTCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KQTPSADZOFBZMJ-QAYKPRTCSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-17(2)9-13-29(14-10-18(3)4)24(32)22(23(31)19(5)6)25(33)30(26(29)34)15-21-20(28(8,36)16-30)11-12-27(21,7)35/h9-10,19-21,32,35-36H,11-16H2,1-8H3/t20-,21+,27-,28-,30+/m1/s1
SMILES:	CC(=CCC1(CC=C(C)C)C(=C(C(=O)C(C)C)C(=O)[C@]2(C1=O)C[C@H]1[C@H]([C@](C2)(C)O)CC[C@@]1(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581593
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[558837]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[558837]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[558837]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[558837]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[558837]

☑ 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 NPC472689 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	192
0.1-0.2	1460
0.2-0.3	6240
0.3-0.4	11706
0.4-0.5	10631
0.5-0.6	7462
0.6-0.7	4178
0.7-0.8	781
0.8-0.85	41
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472690
1.0	High Similarity	NPC477267
1.0	High Similarity	NPC477268
0.8333	Intermediate Similarity	NPC189237
0.8283	Intermediate Similarity	NPC147954
0.8252	Intermediate Similarity	NPC58370
0.8252	Intermediate Similarity	NPC43285
0.8247	Intermediate Similarity	NPC111015
0.82	Intermediate Similarity	NPC474720
0.82	Intermediate Similarity	NPC154072
0.8182	Intermediate Similarity	NPC273269
0.8173	Intermediate Similarity	NPC469508
0.8163	Intermediate Similarity	NPC472485
0.8155	Intermediate Similarity	NPC260268
0.8155	Intermediate Similarity	NPC214264
0.8155	Intermediate Similarity	NPC150531
0.8155	Intermediate Similarity	NPC296945
0.8155	Intermediate Similarity	NPC48733
0.8155	Intermediate Similarity	NPC50692
0.8155	Intermediate Similarity	NPC476027
0.8155	Intermediate Similarity	NPC171137
0.8155	Intermediate Similarity	NPC152695
0.8155	Intermediate Similarity	NPC202167
0.8155	Intermediate Similarity	NPC97202
0.8155	Intermediate Similarity	NPC85829
0.8155	Intermediate Similarity	NPC319077
0.8155	Intermediate Similarity	NPC302607
0.8155	Intermediate Similarity	NPC49958
0.8144	Intermediate Similarity	NPC474807
0.8137	Intermediate Similarity	NPC117185
0.8132	Intermediate Similarity	NPC472684
0.8132	Intermediate Similarity	NPC44963
0.8105	Intermediate Similarity	NPC58532
0.8105	Intermediate Similarity	NPC472677
0.8095	Intermediate Similarity	NPC470257
0.8081	Intermediate Similarity	NPC49371
0.8077	Intermediate Similarity	NPC475060
0.8077	Intermediate Similarity	NPC83744
0.8077	Intermediate Similarity	NPC220229
0.8058	Intermediate Similarity	NPC204833
0.8058	Intermediate Similarity	NPC209502
0.8043	Intermediate Similarity	NPC193347
0.8043	Intermediate Similarity	NPC477270
0.8043	Intermediate Similarity	NPC129080
0.8043	Intermediate Similarity	NPC477271
0.8043	Intermediate Similarity	NPC477269
0.8021	Intermediate Similarity	NPC477943
0.802	Intermediate Similarity	NPC110149
0.8	Intermediate Similarity	NPC329417
0.8	Intermediate Similarity	NPC190554
0.8	Intermediate Similarity	NPC18509
0.8	Intermediate Similarity	NPC27105
0.8	Intermediate Similarity	NPC217201
0.7981	Intermediate Similarity	NPC149047
0.7959	Intermediate Similarity	NPC233118
0.7957	Intermediate Similarity	NPC477373
0.7925	Intermediate Similarity	NPC11710
0.7921	Intermediate Similarity	NPC472687
0.7921	Intermediate Similarity	NPC153776
0.7921	Intermediate Similarity	NPC99657
0.7921	Intermediate Similarity	NPC471331
0.7921	Intermediate Similarity	NPC472730
0.7921	Intermediate Similarity	NPC471330
0.7921	Intermediate Similarity	NPC177680
0.7921	Intermediate Similarity	NPC472729
0.7921	Intermediate Similarity	NPC203388
0.7905	Intermediate Similarity	NPC477916
0.7905	Intermediate Similarity	NPC165873
0.7895	Intermediate Similarity	NPC470345
0.7879	Intermediate Similarity	NPC258674
0.7872	Intermediate Similarity	NPC472480
0.7872	Intermediate Similarity	NPC144258
0.7872	Intermediate Similarity	NPC251170
0.7864	Intermediate Similarity	NPC22388
0.7864	Intermediate Similarity	NPC477915
0.785	Intermediate Similarity	NPC235077
0.7843	Intermediate Similarity	NPC15390
0.7843	Intermediate Similarity	NPC472727
0.7843	Intermediate Similarity	NPC144956
0.7843	Intermediate Similarity	NPC46761
0.7843	Intermediate Similarity	NPC472728
0.7835	Intermediate Similarity	NPC275740
0.7835	Intermediate Similarity	NPC472676
0.7835	Intermediate Similarity	NPC86319
0.7835	Intermediate Similarity	NPC472688
0.783	Intermediate Similarity	NPC65941
0.7826	Intermediate Similarity	NPC279667
0.78	Intermediate Similarity	NPC271195
0.7798	Intermediate Similarity	NPC52634
0.7788	Intermediate Similarity	NPC191892
0.7788	Intermediate Similarity	NPC140723
0.7778	Intermediate Similarity	NPC472928
0.7767	Intermediate Similarity	NPC472924
0.7766	Intermediate Similarity	NPC472492
0.7757	Intermediate Similarity	NPC470615
0.7742	Intermediate Similarity	NPC226068
0.7742	Intermediate Similarity	NPC477372
0.7736	Intermediate Similarity	NPC220974
0.7736	Intermediate Similarity	NPC185
0.7732	Intermediate Similarity	NPC328539
0.7732	Intermediate Similarity	NPC143767
0.7732	Intermediate Similarity	NPC131470
0.7723	Intermediate Similarity	NPC249954
0.7723	Intermediate Similarity	NPC173272
0.7723	Intermediate Similarity	NPC472733
0.7723	Intermediate Similarity	NPC472734
0.7714	Intermediate Similarity	NPC96268
0.7706	Intermediate Similarity	NPC207251
0.77	Intermediate Similarity	NPC114162
0.77	Intermediate Similarity	NPC469819
0.77	Intermediate Similarity	NPC245972
0.77	Intermediate Similarity	NPC196485
0.77	Intermediate Similarity	NPC103527
0.7692	Intermediate Similarity	NPC195290
0.7692	Intermediate Similarity	NPC473424
0.7692	Intermediate Similarity	NPC234892
0.7692	Intermediate Similarity	NPC163249
0.7692	Intermediate Similarity	NPC293753
0.7692	Intermediate Similarity	NPC204450
0.7685	Intermediate Similarity	NPC76084
0.7677	Intermediate Similarity	NPC185936
0.7677	Intermediate Similarity	NPC168027
0.767	Intermediate Similarity	NPC287833
0.767	Intermediate Similarity	NPC83709
0.767	Intermediate Similarity	NPC218383
0.767	Intermediate Similarity	NPC51370
0.7664	Intermediate Similarity	NPC137286
0.7664	Intermediate Similarity	NPC168883
0.7664	Intermediate Similarity	NPC71220
0.766	Intermediate Similarity	NPC133391
0.766	Intermediate Similarity	NPC469325
0.7653	Intermediate Similarity	NPC310010
0.7653	Intermediate Similarity	NPC472970
0.7653	Intermediate Similarity	NPC472971
0.7653	Intermediate Similarity	NPC186688
0.7653	Intermediate Similarity	NPC326627
0.7647	Intermediate Similarity	NPC472732
0.7647	Intermediate Similarity	NPC472731
0.7642	Intermediate Similarity	NPC471333
0.7642	Intermediate Similarity	NPC257353
0.7642	Intermediate Similarity	NPC471332
0.7636	Intermediate Similarity	NPC317210
0.7636	Intermediate Similarity	NPC108721
0.7636	Intermediate Similarity	NPC73300
0.7636	Intermediate Similarity	NPC962
0.7636	Intermediate Similarity	NPC250109
0.7634	Intermediate Similarity	NPC164218
0.7629	Intermediate Similarity	NPC136948
0.7629	Intermediate Similarity	NPC472484
0.7629	Intermediate Similarity	NPC472481
0.7629	Intermediate Similarity	NPC472482
0.7624	Intermediate Similarity	NPC472932
0.7624	Intermediate Similarity	NPC259286
0.7624	Intermediate Similarity	NPC48330
0.7624	Intermediate Similarity	NPC241156
0.7624	Intermediate Similarity	NPC297199
0.7624	Intermediate Similarity	NPC255809
0.7624	Intermediate Similarity	NPC200702
0.7624	Intermediate Similarity	NPC263347
0.7619	Intermediate Similarity	NPC474330
0.7619	Intermediate Similarity	NPC111323
0.7619	Intermediate Similarity	NPC311612
0.7619	Intermediate Similarity	NPC55872
0.7619	Intermediate Similarity	NPC159442
0.7619	Intermediate Similarity	NPC236390
0.7619	Intermediate Similarity	NPC474207
0.7619	Intermediate Similarity	NPC312900
0.7615	Intermediate Similarity	NPC207689
0.7604	Intermediate Similarity	NPC123319
0.7604	Intermediate Similarity	NPC11711
0.7604	Intermediate Similarity	NPC473038
0.7604	Intermediate Similarity	NPC474218
0.7604	Intermediate Similarity	NPC142649
0.7604	Intermediate Similarity	NPC311702
0.7604	Intermediate Similarity	NPC469948
0.7604	Intermediate Similarity	NPC94531
0.76	Intermediate Similarity	NPC470375
0.76	Intermediate Similarity	NPC472930
0.76	Intermediate Similarity	NPC206810
0.76	Intermediate Similarity	NPC475255
0.76	Intermediate Similarity	NPC470376
0.76	Intermediate Similarity	NPC69454
0.7596	Intermediate Similarity	NPC475867
0.7596	Intermediate Similarity	NPC237190
0.7596	Intermediate Similarity	NPC270155
0.7593	Intermediate Similarity	NPC300026
0.7593	Intermediate Similarity	NPC304495
0.7576	Intermediate Similarity	NPC171441
0.7576	Intermediate Similarity	NPC183283
0.7573	Intermediate Similarity	NPC114274
0.7573	Intermediate Similarity	NPC477854
0.757	Intermediate Similarity	NPC472925
0.7568	Intermediate Similarity	NPC238667
0.7568	Intermediate Similarity	NPC473898
0.7568	Intermediate Similarity	NPC326542
0.7551	Intermediate Similarity	NPC471722
0.7551	Intermediate Similarity	NPC471941
0.7551	Intermediate Similarity	NPC53911
0.7551	Intermediate Similarity	NPC472483
0.7551	Intermediate Similarity	NPC474854

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 NPC472689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1910
0.2-0.3	4302
0.3-0.4	1890
0.4-0.5	461
0.5-0.6	175
0.6-0.7	114
0.7-0.8	121
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
0.828	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4223	Phase 3
0.8043	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4755	Approved
0.7979	Intermediate Similarity	NPD5329	Approved
0.7872	Intermediate Similarity	NPD4197	Approved
0.7857	Intermediate Similarity	NPD5281	Approved
0.7857	Intermediate Similarity	NPD5284	Approved
0.785	Intermediate Similarity	NPD4634	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7843	Intermediate Similarity	NPD4700	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7835	Intermediate Similarity	NPD5328	Approved
0.78	Intermediate Similarity	NPD4629	Approved
0.78	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD4202	Approved
0.7767	Intermediate Similarity	NPD5223	Approved
0.7708	Intermediate Similarity	NPD5690	Phase 2
0.7708	Intermediate Similarity	NPD4694	Approved
0.7708	Intermediate Similarity	NPD4689	Approved
0.7708	Intermediate Similarity	NPD5205	Approved
0.7708	Intermediate Similarity	NPD4688	Approved
0.7708	Intermediate Similarity	NPD4690	Approved
0.7708	Intermediate Similarity	NPD4138	Approved
0.7708	Intermediate Similarity	NPD5280	Approved
0.7708	Intermediate Similarity	NPD4693	Phase 3
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD6079	Approved
0.7653	Intermediate Similarity	NPD4753	Phase 2
0.7642	Intermediate Similarity	NPD6675	Approved
0.7642	Intermediate Similarity	NPD5739	Approved
0.7642	Intermediate Similarity	NPD7128	Approved
0.7642	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7619	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD4754	Approved
0.7593	Intermediate Similarity	NPD6372	Approved
0.7593	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD5696	Approved
0.7549	Intermediate Similarity	NPD4697	Phase 3
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.7477	Intermediate Similarity	NPD4768	Approved
0.7477	Intermediate Similarity	NPD6008	Approved
0.7477	Intermediate Similarity	NPD4767	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7451	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5701	Approved
0.7407	Intermediate Similarity	NPD5697	Approved
0.7391	Intermediate Similarity	NPD6054	Approved
0.7391	Intermediate Similarity	NPD6059	Approved
0.7379	Intermediate Similarity	NPD5221	Approved
0.7379	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5222	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD5091	Approved
0.734	Intermediate Similarity	NPD4195	Approved
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD5128	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD6011	Approved
0.7321	Intermediate Similarity	NPD4632	Approved
0.7308	Intermediate Similarity	NPD6084	Phase 2
0.7308	Intermediate Similarity	NPD6083	Phase 2
0.7308	Intermediate Similarity	NPD5173	Approved
0.73	Intermediate Similarity	NPD6904	Approved
0.73	Intermediate Similarity	NPD6080	Approved
0.73	Intermediate Similarity	NPD6673	Approved
0.7297	Intermediate Similarity	NPD8130	Phase 1
0.7297	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6847	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7282	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7265	Intermediate Similarity	NPD6370	Approved
0.7241	Intermediate Similarity	NPD6319	Approved
0.7234	Intermediate Similarity	NPD3617	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7232	Intermediate Similarity	NPD8297	Approved
0.7228	Intermediate Similarity	NPD4096	Approved
0.7216	Intermediate Similarity	NPD4788	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.7188	Intermediate Similarity	NPD4692	Approved
0.7188	Intermediate Similarity	NPD4139	Approved
0.7184	Intermediate Similarity	NPD6001	Approved
0.7179	Intermediate Similarity	NPD6016	Approved
0.7179	Intermediate Similarity	NPD6015	Approved
0.7157	Intermediate Similarity	NPD6050	Approved
0.7143	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD6009	Approved
0.7119	Intermediate Similarity	NPD5988	Approved
0.7087	Intermediate Similarity	NPD5133	Approved
0.7087	Intermediate Similarity	NPD6399	Phase 3
0.7083	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD4695	Discontinued
0.7059	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD5692	Phase 3
0.703	Intermediate Similarity	NPD4518	Approved
0.703	Intermediate Similarity	NPD5208	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD5279	Phase 3
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD5693	Phase 1
0.699	Remote Similarity	NPD5694	Approved
0.6967	Remote Similarity	NPD6033	Approved
0.6967	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD5167	Approved
0.6957	Remote Similarity	NPD4243	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD6335	Approved
0.6917	Remote Similarity	NPD7604	Phase 2
0.6897	Remote Similarity	NPD6274	Approved
0.6891	Remote Similarity	NPD5983	Phase 2
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.6863	Remote Similarity	NPD5737	Approved
0.6863	Remote Similarity	NPD6672	Approved
0.6863	Remote Similarity	NPD6903	Approved
0.6863	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4747	Approved
0.6838	Remote Similarity	NPD6317	Approved
0.6832	Remote Similarity	NPD4623	Approved
0.6832	Remote Similarity	NPD4519	Discontinued
0.6827	Remote Similarity	NPD7515	Phase 2
0.6822	Remote Similarity	NPD7902	Approved
0.6809	Remote Similarity	NPD5733	Approved
0.6809	Remote Similarity	NPD4785	Approved
0.6809	Remote Similarity	NPD4784	Approved
0.6803	Remote Similarity	NPD6336	Discontinued
0.6786	Remote Similarity	NPD6614	Approved
0.6783	Remote Similarity	NPD6053	Discontinued
0.678	Remote Similarity	NPD6313	Approved
0.678	Remote Similarity	NPD6314	Approved
0.6778	Remote Similarity	NPD7331	Phase 2
0.6768	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3573	Approved
0.6759	Remote Similarity	NPD7638	Approved
0.675	Remote Similarity	NPD6909	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6908	Approved
0.6739	Remote Similarity	NPD4137	Phase 3
0.6735	Remote Similarity	NPD7525	Registered
0.6726	Remote Similarity	NPD5168	Approved
0.6723	Remote Similarity	NPD4522	Approved
0.6698	Remote Similarity	NPD7748	Approved
0.6698	Remote Similarity	NPD5282	Discontinued
0.6697	Remote Similarity	NPD7640	Approved
0.6697	Remote Similarity	NPD7639	Approved
0.6695	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD4691	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6636	Remote Similarity	NPD5654	Approved
0.6635	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD4687	Approved
0.6596	Remote Similarity	NPD5276	Approved
0.6574	Remote Similarity	NPD7614	Phase 1
0.6562	Remote Similarity	NPD4190	Phase 3
0.6562	Remote Similarity	NPD5275	Approved
0.6542	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7900	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