NPASS Compound

Structure

NPC159748 OpenBabel07101718192D 33 36 0 0 1 0 0 0 0 0999 V2000 2.6351 -3.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3561 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3291 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9398 -0.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3833 -2.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 1.9459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0557 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 3.4054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0713 -1.6953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8983 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4435 -2.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 32 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 29 2 0 0 0 0 17 33 1 0 0 0 0 18 30 2 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 27 1 1 0 0 0 23 28 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.3
Volume:	492.024
LogP:	4.872
LogD:	4.0
LogS:	-4.434
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.797
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	2.156387927243486e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	57.89157485961914%
Volume Distribution (VD):	1.885
Pgp-substrate:	44.67599868774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.208
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.65
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	7.268
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.967
Carcinogencity:	0.673
Eye Corrosion:	0.565
Eye Irritation:	0.271
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC159748

Natural Product ID:	NPC159748
*Common Name:**	Methyl (1S,4As,4Bs,6As,10Ar,10Bs,12As)-10A-(Acetyloxymethyl)-1-Formyl-4B,7,7,12A-Tetramethyl-1,4,4A,5,6,6A,8,9,10,10B,11,12-Dodecahydrochrysene-2-Carboxylate
IUPAC Name:	methyl (1S,4aS,4bS,6aS,10aR,10bS,12aS)-10a-(acetyloxymethyl)-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,5,6,6a,8,9,10,10b,11,12-dodecahydrochrysene-2-carboxylate
Synonyms:
Standard InCHIKey:	ASDDNTIFAUVZTF-GHVIDDCHSA-N
Standard InCHI:	InChI=1S/C28H42O5/c1-18(30)33-17-28-13-7-12-25(2,3)21(28)10-15-27(5)22-9-8-19(24(31)32-6)20(16-29)26(22,4)14-11-23(27)28/h8,16,20-23H,7,9-15,17H2,1-6H3/t20-,21+,22-,23+,26-,27+,28-/m1/s1
SMILES:	CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3CC=C([C@@H](C=O)[C@@]3(C)CC[C@H]21)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573363
PubChem CID:	25158955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	3.7	ug.mL-1	PMID[499700]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[499700]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[499700]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[499700]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[499700]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[499700]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[499700]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[499700]

☑ 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 NPC159748 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	229
0.1-0.2	1480
0.2-0.3	5079
0.3-0.4	13291
0.4-0.5	9668
0.5-0.6	7103
0.6-0.7	4701
0.7-0.8	1087
0.8-0.85	47
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC101651
0.9318	High Similarity	NPC151722
0.9176	High Similarity	NPC2709
0.8791	High Similarity	NPC269729
0.8764	High Similarity	NPC469546
0.875	High Similarity	NPC477228
0.871	High Similarity	NPC204054
0.871	High Similarity	NPC257726
0.8696	High Similarity	NPC274417
0.8605	High Similarity	NPC200513
0.8587	High Similarity	NPC476415
0.8523	High Similarity	NPC189311
0.8506	High Similarity	NPC22611
0.8462	Intermediate Similarity	NPC328141
0.8444	Intermediate Similarity	NPC226863
0.8438	Intermediate Similarity	NPC310981
0.8438	Intermediate Similarity	NPC63249
0.8391	Intermediate Similarity	NPC186276
0.8391	Intermediate Similarity	NPC142683
0.8372	Intermediate Similarity	NPC474956
0.837	Intermediate Similarity	NPC230064
0.8352	Intermediate Similarity	NPC477973
0.8352	Intermediate Similarity	NPC174342
0.8352	Intermediate Similarity	NPC168131
0.8351	Intermediate Similarity	NPC134077
0.8333	Intermediate Similarity	NPC475385
0.8333	Intermediate Similarity	NPC475392
0.8333	Intermediate Similarity	NPC475202
0.8316	Intermediate Similarity	NPC476768
0.8315	Intermediate Similarity	NPC65661
0.8295	Intermediate Similarity	NPC307258
0.828	Intermediate Similarity	NPC476416
0.828	Intermediate Similarity	NPC169343
0.828	Intermediate Similarity	NPC474185
0.8276	Intermediate Similarity	NPC229584
0.8276	Intermediate Similarity	NPC14203
0.8276	Intermediate Similarity	NPC40228
0.8265	Intermediate Similarity	NPC254202
0.8261	Intermediate Similarity	NPC469595
0.8261	Intermediate Similarity	NPC212679
0.8261	Intermediate Similarity	NPC220454
0.8261	Intermediate Similarity	NPC198818
0.8242	Intermediate Similarity	NPC472302
0.8222	Intermediate Similarity	NPC220478
0.8211	Intermediate Similarity	NPC319692
0.8211	Intermediate Similarity	NPC325960
0.8191	Intermediate Similarity	NPC470697
0.8172	Intermediate Similarity	NPC65513
0.8163	Intermediate Similarity	NPC40918
0.8161	Intermediate Similarity	NPC104545
0.8161	Intermediate Similarity	NPC195424
0.8152	Intermediate Similarity	NPC5509
0.8152	Intermediate Similarity	NPC284561
0.8125	Intermediate Similarity	NPC10057
0.8111	Intermediate Similarity	NPC30984
0.8111	Intermediate Similarity	NPC86316
0.8111	Intermediate Similarity	NPC106416
0.8105	Intermediate Similarity	NPC33473
0.8095	Intermediate Similarity	NPC211641
0.8085	Intermediate Similarity	NPC475657
0.8081	Intermediate Similarity	NPC476889
0.8081	Intermediate Similarity	NPC282233
0.8081	Intermediate Similarity	NPC95585
0.8065	Intermediate Similarity	NPC476437
0.8065	Intermediate Similarity	NPC8062
0.8065	Intermediate Similarity	NPC476369
0.8061	Intermediate Similarity	NPC93744
0.8061	Intermediate Similarity	NPC476888
0.8043	Intermediate Similarity	NPC224145
0.8041	Intermediate Similarity	NPC478056
0.8041	Intermediate Similarity	NPC471966
0.8023	Intermediate Similarity	NPC472300
0.8023	Intermediate Similarity	NPC316500
0.8	Intermediate Similarity	NPC84893
0.8	Intermediate Similarity	NPC470297
0.8	Intermediate Similarity	NPC189616
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC312660
0.8	Intermediate Similarity	NPC91010
0.8	Intermediate Similarity	NPC318515
0.8	Intermediate Similarity	NPC477130
0.798	Intermediate Similarity	NPC476890
0.7959	Intermediate Similarity	NPC470906
0.7957	Intermediate Similarity	NPC184663
0.7957	Intermediate Similarity	NPC177141
0.7955	Intermediate Similarity	NPC477057
0.7955	Intermediate Similarity	NPC267517
0.7941	Intermediate Similarity	NPC275539
0.7941	Intermediate Similarity	NPC189075
0.7938	Intermediate Similarity	NPC151681
0.7938	Intermediate Similarity	NPC121402
0.7938	Intermediate Similarity	NPC170131
0.7938	Intermediate Similarity	NPC224356
0.7938	Intermediate Similarity	NPC132753
0.7938	Intermediate Similarity	NPC175351
0.7935	Intermediate Similarity	NPC46912
0.7935	Intermediate Similarity	NPC162107
0.7931	Intermediate Similarity	NPC260385
0.7931	Intermediate Similarity	NPC59436
0.7931	Intermediate Similarity	NPC4827
0.7931	Intermediate Similarity	NPC280654
0.7931	Intermediate Similarity	NPC110094
0.7917	Intermediate Similarity	NPC293052
0.7917	Intermediate Similarity	NPC183012
0.7912	Intermediate Similarity	NPC474013
0.79	Intermediate Similarity	NPC478057
0.79	Intermediate Similarity	NPC476770
0.7895	Intermediate Similarity	NPC472303
0.7889	Intermediate Similarity	NPC200752
0.7889	Intermediate Similarity	NPC193198
0.7882	Intermediate Similarity	NPC128346
0.7882	Intermediate Similarity	NPC166797
0.7882	Intermediate Similarity	NPC219232
0.7872	Intermediate Similarity	NPC51486
0.7872	Intermediate Similarity	NPC273199
0.7872	Intermediate Similarity	NPC469372
0.7872	Intermediate Similarity	NPC76286
0.7865	Intermediate Similarity	NPC471898
0.7865	Intermediate Similarity	NPC90055
0.7865	Intermediate Similarity	NPC474955
0.7865	Intermediate Similarity	NPC278459
0.7864	Intermediate Similarity	NPC112457
0.7857	Intermediate Similarity	NPC98868
0.7857	Intermediate Similarity	NPC194196
0.7857	Intermediate Similarity	NPC176845
0.7849	Intermediate Similarity	NPC477128
0.7849	Intermediate Similarity	NPC474845
0.7849	Intermediate Similarity	NPC215831
0.7849	Intermediate Similarity	NPC24816
0.7849	Intermediate Similarity	NPC474474
0.7843	Intermediate Similarity	NPC110496
0.7841	Intermediate Similarity	NPC327674
0.7841	Intermediate Similarity	NPC199595
0.7835	Intermediate Similarity	NPC154526
0.7835	Intermediate Similarity	NPC472362
0.7835	Intermediate Similarity	NPC472363
0.7835	Intermediate Similarity	NPC471039
0.7835	Intermediate Similarity	NPC112654
0.7826	Intermediate Similarity	NPC168248
0.7826	Intermediate Similarity	NPC9892
0.7826	Intermediate Similarity	NPC329943
0.7826	Intermediate Similarity	NPC91525
0.7826	Intermediate Similarity	NPC195640
0.7826	Intermediate Similarity	NPC324063
0.7826	Intermediate Similarity	NPC10005
0.7822	Intermediate Similarity	NPC472868
0.7816	Intermediate Similarity	NPC471899
0.7816	Intermediate Similarity	NPC107039
0.7816	Intermediate Similarity	NPC471897
0.7812	Intermediate Similarity	NPC74751
0.7812	Intermediate Similarity	NPC294266
0.7812	Intermediate Similarity	NPC471040
0.7802	Intermediate Similarity	NPC248758
0.7802	Intermediate Similarity	NPC96095
0.7802	Intermediate Similarity	NPC149869
0.7802	Intermediate Similarity	NPC71626
0.7802	Intermediate Similarity	NPC30486
0.7802	Intermediate Similarity	NPC156981
0.7791	Intermediate Similarity	NPC244166
0.7791	Intermediate Similarity	NPC65650
0.7789	Intermediate Similarity	NPC470113
0.7789	Intermediate Similarity	NPC49420
0.7789	Intermediate Similarity	NPC477783
0.7789	Intermediate Similarity	NPC218301
0.7789	Intermediate Similarity	NPC476187
0.7789	Intermediate Similarity	NPC289479
0.7789	Intermediate Similarity	NPC473944
0.7778	Intermediate Similarity	NPC178676
0.7778	Intermediate Similarity	NPC470813
0.7778	Intermediate Similarity	NPC201406
0.7778	Intermediate Similarity	NPC477720
0.7778	Intermediate Similarity	NPC174314
0.7767	Intermediate Similarity	NPC473483
0.7767	Intermediate Similarity	NPC89171
0.7767	Intermediate Similarity	NPC476802
0.7766	Intermediate Similarity	NPC475049
0.7766	Intermediate Similarity	NPC251528
0.7766	Intermediate Similarity	NPC281524
0.7766	Intermediate Similarity	NPC474700
0.7766	Intermediate Similarity	NPC73995
0.7766	Intermediate Similarity	NPC285982
0.7765	Intermediate Similarity	NPC144947
0.7755	Intermediate Similarity	NPC84335
0.7755	Intermediate Similarity	NPC473456
0.7755	Intermediate Similarity	NPC253826
0.7755	Intermediate Similarity	NPC38530
0.7753	Intermediate Similarity	NPC37038
0.7745	Intermediate Similarity	NPC1679
0.7732	Intermediate Similarity	NPC127197
0.7732	Intermediate Similarity	NPC281134
0.7732	Intermediate Similarity	NPC139459
0.7732	Intermediate Similarity	NPC280877
0.7727	Intermediate Similarity	NPC115515
0.7727	Intermediate Similarity	NPC198240
0.7723	Intermediate Similarity	NPC176883
0.7723	Intermediate Similarity	NPC95899
0.7723	Intermediate Similarity	NPC120321
0.7723	Intermediate Similarity	NPC112009
0.7723	Intermediate Similarity	NPC180204
0.7717	Intermediate Similarity	NPC177932

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 NPC159748 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	1658
0.2-0.3	3887
0.3-0.4	2243
0.4-0.5	732
0.5-0.6	249
0.6-0.7	141
0.7-0.8	28
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD4752	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7900	Approved
0.8043	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7902	Approved
0.7849	Intermediate Similarity	NPD6672	Approved
0.7849	Intermediate Similarity	NPD5737	Approved
0.7826	Intermediate Similarity	NPD6684	Approved
0.7826	Intermediate Similarity	NPD7334	Approved
0.7826	Intermediate Similarity	NPD5330	Approved
0.7826	Intermediate Similarity	NPD7521	Approved
0.7826	Intermediate Similarity	NPD7146	Approved
0.7826	Intermediate Similarity	NPD6409	Approved
0.7812	Intermediate Similarity	NPD7748	Approved
0.7717	Intermediate Similarity	NPD1694	Approved
0.766	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD5693	Phase 1
0.7604	Intermediate Similarity	NPD7515	Phase 2
0.7553	Intermediate Similarity	NPD3573	Approved
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7638	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.7396	Intermediate Similarity	NPD6673	Approved
0.7386	Intermediate Similarity	NPD8039	Approved
0.7374	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7732	Phase 3
0.7228	Intermediate Similarity	NPD6083	Phase 2
0.7228	Intermediate Similarity	NPD6084	Phase 2
0.7216	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6051	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7157	Intermediate Similarity	NPD5696	Approved
0.7113	Intermediate Similarity	NPD5208	Approved
0.7103	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD6098	Approved
0.7071	Intermediate Similarity	NPD8034	Phase 2
0.7071	Intermediate Similarity	NPD6050	Approved
0.7071	Intermediate Similarity	NPD8035	Phase 2
0.703	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4225	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.697	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD5692	Phase 3
0.6961	Remote Similarity	NPD4697	Phase 3
0.6961	Remote Similarity	NPD7614	Phase 1
0.6931	Remote Similarity	NPD6001	Approved
0.6909	Remote Similarity	NPD6650	Approved
0.6909	Remote Similarity	NPD6649	Approved
0.6907	Remote Similarity	NPD3618	Phase 1
0.69	Remote Similarity	NPD5694	Approved
0.6881	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD6008	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6742	Remote Similarity	NPD4691	Approved
0.6735	Remote Similarity	NPD4623	Approved
0.6735	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6079	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6733	Remote Similarity	NPD5281	Approved
0.6729	Remote Similarity	NPD6052	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6701	Remote Similarity	NPD4786	Approved
0.6701	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD4753	Phase 2
0.67	Remote Similarity	NPD5328	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6699	Remote Similarity	NPD5210	Approved
0.6697	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5329	Approved
0.6629	Remote Similarity	NPD4137	Phase 3
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6604	Remote Similarity	NPD6404	Discontinued
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6411	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6556	Remote Similarity	NPD4747	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6549	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD6412	Phase 2
0.6538	Remote Similarity	NPD5654	Approved
0.6531	Remote Similarity	NPD4197	Approved
0.6522	Remote Similarity	NPD4058	Approved
0.6495	Remote Similarity	NPD5209	Approved
0.6491	Remote Similarity	NPD6858	Approved
0.6491	Remote Similarity	NPD7094	Approved
0.6476	Remote Similarity	NPD5222	Approved
0.6476	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5221	Approved
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4788	Approved
0.6421	Remote Similarity	NPD3617	Approved
0.6415	Remote Similarity	NPD5173	Approved
0.6415	Remote Similarity	NPD5959	Approved
0.6404	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD4138	Approved
0.64	Remote Similarity	NPD4688	Approved
0.64	Remote Similarity	NPD5205	Approved
0.64	Remote Similarity	NPD4689	Approved
0.64	Remote Similarity	NPD5690	Phase 2
0.64	Remote Similarity	NPD5279	Phase 3
0.64	Remote Similarity	NPD4690	Approved
0.64	Remote Similarity	NPD4693	Phase 3
0.6392	Remote Similarity	NPD8028	Phase 2
0.6381	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6868	Approved
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6354	Remote Similarity	NPD7645	Phase 2
0.6346	Remote Similarity	NPD5778	Approved
0.6346	Remote Similarity	NPD5779	Approved
0.6346	Remote Similarity	NPD4202	Approved
0.6344	Remote Similarity	NPD5733	Approved
0.633	Remote Similarity	NPD5211	Phase 2
0.6321	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD46	Approved
0.6311	Remote Similarity	NPD6698	Approved
0.6304	Remote Similarity	NPD5777	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6283	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8328	Phase 3
0.6271	Remote Similarity	NPD6335	Approved
0.6262	Remote Similarity	NPD4755	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.6238	Remote Similarity	NPD4694	Approved
0.6238	Remote Similarity	NPD5280	Approved
0.6218	Remote Similarity	NPD7100	Approved
0.6218	Remote Similarity	NPD7101	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6317	Approved
0.6186	Remote Similarity	NPD4195	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4687	Approved
0.6154	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4700	Approved
0.6139	Remote Similarity	NPD5363	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD6314	Approved
0.6129	Remote Similarity	NPD5276	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6116	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7503	Approved
0.6095	Remote Similarity	NPD7637	Suspended
0.6087	Remote Similarity	NPD6371	Approved
0.6083	Remote Similarity	NPD7516	Approved
0.6082	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7736	Approved
0.6068	Remote Similarity	NPD8133	Approved
0.6063	Remote Similarity	NPD7260	Phase 2
0.6058	Remote Similarity	NPD1695	Approved
0.6055	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD5091	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