NPASS Compound

Natural Product: NPC480937

Natural Product ID	NPC480937
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MAXPHAYYQCXJEX-WARPVFOQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 101106 0 0 0 0 0 0 0 0999 V2000 -6.5993 3.3237 -0.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6898 1.7853 -0.4050 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7750 1.4759 -1.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1033 1.4056 0.9719 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1456 0.5310 1.7029 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5362 -0.5530 0.8452 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6775 -1.5344 0.5363 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1906 -2.0661 1.7243 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9416 -0.0601 -0.4105 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3937 1.2714 -0.8893 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4348 -0.0418 -0.4075 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 0.5771 -1.4374 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4002 0.7128 -1.6333 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6167 0.1040 -0.5211 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8430 -0.0559 -0.8214 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1489 -0.5215 -2.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4502 1.3530 -0.6932 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9241 1.3240 -0.8708 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6659 0.3642 0.0259 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9453 -0.9189 0.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2786 -1.2819 1.7659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4909 -2.0679 -0.5223 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4622 -0.8355 0.2783 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8563 -2.2190 0.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5662 -1.9734 0.9072 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3145 -1.1361 -0.0655 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7720 -2.0140 -1.2043 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5953 -0.6492 0.6328 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2849 0.4126 1.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2692 -1.7855 1.3537 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6131 -1.3110 1.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0442 -1.5384 2.8753 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8841 0.1432 -0.6130 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9126 0.7294 0.1082 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8927 -0.3132 0.5051 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2828 0.2158 0.7861 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7647 1.1247 -0.2870 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6655 1.5374 -1.2093 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5143 0.6433 -2.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5288 0.2930 -3.0619 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3022 0.1291 -2.8030 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4829 1.7956 -0.5859 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2590 2.2882 0.3379 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1475 -0.8799 0.8969 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4643 -0.8663 1.7358 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3318 3.7644 0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5717 3.6351 -0.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7716 3.6797 -1.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5494 0.5120 -1.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8982 2.2689 -2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7229 1.3724 -0.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3292 2.2773 1.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0936 0.8673 0.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6942 0.0249 2.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3285 1.1013 2.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4672 -1.0485 -0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3139 -2.3972 -0.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9657 -1.4691 1.9667 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1938 -0.8051 -1.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5960 2.0412 -0.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4503 1.2833 -2.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4608 1.0402 -2.2335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1946 1.8238 -1.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1628 0.3498 -2.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6728 0.8335 0.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8538 0.2730 -2.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 -1.5204 -2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2546 -0.5997 -2.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0149 2.0263 -1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2271 1.6722 0.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2267 1.1509 -1.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3072 2.3487 -0.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8791 0.9280 0.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0286 -2.1264 1.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.5333 2.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8010 -0.4253 2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0219 -2.8339 0.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2772 -1.6778 -1.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6962 -2.6108 -1.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1446 -0.3095 1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7281 -2.7197 -0.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3771 -2.7999 1.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4542 -1.5660 1.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0764 -2.9598 0.9751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8668 -2.2636 -1.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6240 -1.5830 -2.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2532 -3.0121 -1.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0694 0.3482 2.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3875 1.4416 1.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3283 0.2554 2.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 -2.7331 0.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6837 -1.9497 2.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5074 1.2077 1.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9068 -1.1718 -0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2525 0.7129 1.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6241 0.7144 -0.8549 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0036 2.5341 -1.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2235 -0.7498 -3.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5306 2.8049 0.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6247 -1.0105 0.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8095 -0.3342 2.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 7 8 1 0 6 9 1 0 9 10 1 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 2 0 19 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 37 43 1 0 36 44 1 0 35 45 1 0 10 2 1 0 28 11 1 0 42 34 1 0 31 6 1 0 26 14 1 0 23 15 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 9 59 1 6 10 60 1 0 10 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 1 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 18 71 1 0 18 72 1 0 19 73 1 1 21 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 22 79 1 0 23 80 1 1 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 27 86 1 0 27 87 1 0 29 88 1 0 29 89 1 0 29 90 1 0 30 91 1 0 30 92 1 0 34 93 1 1 35 94 1 6 36 95 1 1 37 96 1 6 38 97 1 6 41 98 1 0 43 99 1 0 44100 1 0 45101 1 0 M END

Standard InCHIKey	MAXPHAYYQCXJEX-WARPVFOQSA-N
Standard InCHI	InChI=1S/C36H56O9/c1-31(2)14-15-36(18-37)20(16-31)19-8-9-22-33(5)12-11-24(44-30-27(41)25(39)26(40)28(45-30)29(42)43)32(3,4)21(33)10-13-34(22,6)35(19,7)17-23(36)38/h8,20-22,24-28,30,37,39-41H,9-18H2,1-7H3,(H,42,43)/t20-,21-,22+,24-,25-,26-,27+,28-,30+,33-,34+,35+,36+/m0/s1
SMILES	CC1(C)CC[C@@]2(CO)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.39	Volume:	651.076 ? Van der Waals volume.
Dense:	0.971	LogP:	2.865 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.915 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.192 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	34.0
TPSA:	153.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.226	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.426	Fsp³:	0.889
MCE-18:	129.882 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.961	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.028 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.843	MDCK Permeability:	-5.154
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.028	30% Bioavailability (F30%):	0.029
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.954
Plasma Protein Binding (PPB):	83.238%	Volume Distribution (VD):	-0.613
Fu:	11.935% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.3	BCRP inhibitor:	0.005
BSEP inhibitor:	0.383

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.928	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.021	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.023
HLM stability:	0.003 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.579

Half-life (T1/2):

2.149

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.639	Drug-induced Liver Injury (DILI):	0.912
AMES Toxicity:	0.635	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.08	Skin Sensitization:	0.993
Carcinogencity:	0.546	Eye Corrosion:	0.0
Eye Irritation:	0.04	Respiratory Toxicity:	0.192
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.924
Hematotoxicity:	0.687	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.903	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.187	Hek293 Cytotoxicity:	0.184
BCF:	0.785 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.613 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.229 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.43 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16926516]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[22834923]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30395460]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32569471]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065796]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23380	Camellia japonica	Species	Theaceae	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	Organism Name	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
Activity	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT804	Cell line	HT-22	Mus musculus	Activity	=	55.5	%	PMID[32569471]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC480937 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18006
0.1-0.2	27164
0.2-0.3	3533
0.3-0.4	804
0.4-0.5	280
0.5-0.6	55
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7191	Intermediate Similarity	NPC480943
0.7111	Intermediate Similarity	NPC480938
0.7021	Intermediate Similarity	NPC157868
0.6932	Remote Similarity	NPC286347
0.6742	Remote Similarity	NPC224121
0.6495	Remote Similarity	NPC473884
0.62	Remote Similarity	NPC242840
0.617	Remote Similarity	NPC294112
0.604	Remote Similarity	NPC75417
0.596	Remote Similarity	NPC309780
0.5922	Remote Similarity	NPC251768
0.5922	Remote Similarity	NPC159309
0.5922	Remote Similarity	NPC86222
0.5769	Remote Similarity	NPC40775
0.5769	Remote Similarity	NPC44716
0.5755	Remote Similarity	NPC64715
0.5701	Remote Similarity	NPC114484
0.5648	Remote Similarity	NPC301449
0.5648	Remote Similarity	NPC601290
0.5619	Remote Similarity	NPC11551
0.5588	Remote Similarity	NPC482748
0.5577	Remote Similarity	NPC192791
0.5566	Remote Similarity	NPC475591
0.5566	Remote Similarity	NPC236870
0.5534	Remote Similarity	NPC472949
0.5514	Remote Similarity	NPC611191
0.5495	Remote Similarity	NPC11242
0.5481	Remote Similarity	NPC475171
0.5474	Remote Similarity	NPC606107
0.5463	Remote Similarity	NPC302887
0.5455	Remote Similarity	NPC160452
0.5455	Remote Similarity	NPC482752
0.5437	Remote Similarity	NPC114441
0.5413	Remote Similarity	NPC281148
0.5385	Remote Similarity	NPC6377
0.5385	Remote Similarity	NPC208381
0.537	Remote Similarity	NPC31193
0.5357	Remote Similarity	NPC480936
0.5315	Remote Similarity	NPC120116
0.5312	Remote Similarity	NPC283849
0.5268	Remote Similarity	NPC187290
0.5268	Remote Similarity	NPC477194
0.5204	Remote Similarity	NPC31839
0.5189	Remote Similarity	NPC22956
0.5189	Remote Similarity	NPC482717
0.5179	Remote Similarity	NPC477193
0.5143	Remote Similarity	NPC173583
0.5138	Remote Similarity	NPC482722
0.5138	Remote Similarity	NPC471963
0.5138	Remote Similarity	NPC118440
0.5133	Remote Similarity	NPC469947
0.5133	Remote Similarity	NPC480948
0.5126	Remote Similarity	NPC4749
0.5098	Remote Similarity	NPC214484
0.5093	Remote Similarity	NPC605226
0.5089	Remote Similarity	NPC477075
0.5088	Remote Similarity	NPC480939
0.5083	Remote Similarity	NPC21691
0.5057	Remote Similarity	NPC191965
0.5049	Remote Similarity	NPC1046
0.5048	Remote Similarity	NPC235405
0.5048	Remote Similarity	NPC482750
0.5047	Remote Similarity	NPC482746
0.5045	Remote Similarity	NPC95437

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC480937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5868
0.1-0.2	3218
0.2-0.3	57
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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